Laurence Grimaud

Printer-friendly version

Summary

      Biography

      Current Research Interests

      The Group

      Publications

      Chapters in collective international books

 

 


Biography

ORCID 0000-0003-3904-1822

 

  • Appointments

2016             Research Director at CNRS (DR 2) at the ENS Paris – UMR 7203

2012             Researcher at CNRS (CR 1) at the ENS Paris – UMR 8640

2010             Researcher at CNRS (CR 1) at the Ecole Polytechnique -UMR 7652

2006             Habilitation à diriger des recherches (HDR, Paris XI)

1999-2010    Assistant Professeur at the ENSTA with Pr Laurent El Kaïm

 

  • Education

 

1996-1999      Ph. D. in Organic Chemistry at Ecole Polytechnique under the supervision of Dr J. Prunet 

1995-1996      Agregation de Sciences Physiques – Option Chimie

1994-1995      MS of Organic Chemistry at UPMC 

1993                BsC s at the Ecole Normale Supérieure (ENS) of Paris

 

 


Current Research Interests

 

           Mechanistic Studies of Metal-Catalyzed Processes and Methodology in Isocyanide Chemistry

 

 

 

 

 


The Group

 

  • PhD students

Pierre-Adrien Payard (co-direction with Dr M. Pera-Titus)

Na Pan

Yinan Fan

Aurélien Bailly (co-direction with Dr S. Prévost)

Khaoula Jaouadi (co-direction with Pr L. Fensterbank)

 

  • Master students

Emile Escoudé

 

Summertime in 2018

 

The team in 2017

 

Aude and Indira awarded by L'oréal-Unesco in 2017

 

Baptiste and Pierre-Adrien for the SCF (https://www.youtube.com/watch?v=keXcypIvs6U)

 

  • Former PhD Students

Direction

Dr Baptiste Haddou (defense July 2018)

Co-direction with Dr Ilaria Ciofini (http://www.chimie-paristech.fr/labos/LECA/Research/site_msc/equipe.html)

Dr Luca Alessandro Perego (defense february 2018)

Dr Indira Fabre (defense July 2017)

 

Co-direction with Pr P. Fleurat-Lessard 

Dr Nicolas Chéron (2011)

 

Co-direction with Dr P. Dauban

Dr Elodie Martinand-Lurin (2015)

 

Co-direction with Pr L. El Kaim (http://ucp.ensta-paristech.fr/equipe/elkaim.php)

Dr Aude Nyadanu (2018)

Dr Madjid Ait-Sidhoum (2015)

Dr Romain Ramozzi (2013)

Dr Patil Pravin (2012)

Dr Caroline Ronsseray (2011)

Dr Anaëlle Barthelon (2011)

Dr Marion Gizzi (2010)

Dr Aurélie Schiltz (2010)

Dr Simon Wagschal (2010)

Dr Didier Coffinier (2010)

Dr Julie Oble (2007)

Dr Marie Gizolme (2007)

Dr Emeline Vedrenne (2006)

Dr Laetitia Gaultier (2005)

Dr Frédérique Royer (2004)

Dr Valérie Michaut (2003)

Dr Cornélia Tirla (2003)

 

  • Former Post-doc

Dr Hakim Lakmini (ENS)

Dr Marta Menes-Arzate (ENSTA)

Dr Damien Cartigny (ENSTA)

Dr Srinivas Purumandla Reddy (ENSTA)

 


Publications

2019

111. Electroactive fluorescent false neurotransmitter FFN102 partially replaces dopamine in PC12 cell vesicles. Hu, L.; Savy, A.; Grimaud, L.; Guille-Collignon, M.; Lemaître, F.; Amatore, C.; Delacotte, J. Biophys. Chem. 2019, 245, 1-5. (DOI: 10.1016/j.bpc.2018.11.001)

 

110. Metformin reveals a mitochondrial copper addiction of mesenchymal cancer cells. Müller, S.; Versini, A.; Sindikubwabo, F.; Belthier, G.; Niyomchon, S.; Pannequin, J.; Grimaud, L.; Cañeque, T.; Rodriguez R.  PLOS ONE 2018, accepted, DOI: 10.1371/journal.pone.0206764.

 

109. From Benzofurans to Indoles: Palladium-Catalyzed Reductive Ring-Opening and Closure via β-Phenoxide Elimination. Perego, L. A.; Wagschal, S.; Grüber, R.; Fleurat-Lessard, P.; El Kaïm, L.; Grimaud, L. Adv. Synth. Cat.  2019361, 151-159(DOI 10.1002/adsc.201801225).

 

2018

108. Direct Amination of Alcohols Catalyzed by Aluminum Triflate: an Experimental and Computational Study. Payard, P. A.; Gu, Q.; Guo, W.; Wang, Q.; Corbet, M.; Michel, C.; Sautet, P.; Grimaud, L.; Wischert, R.; Pera‐Titus, M. Chem. Eur. J. 2018, 53, 14146-14153 (DOI 10.1002/chem.201801492).


107. Taming Nickel-Catalyzed Suzuki-Miyaura Coupling: a Mechanistic Focus on Boron-to-Nickel Transmetalation. Payard, P. A.; Perego, L. A.; Ciofini, I.; Grimaud, L. ACS catal. 20188, 4812-4823. DOI: 10.1021/acscatal.8b00933

106. 4-Aminopyrimidine Libraries from the Ugi-Smiles Reaction of Thiouracil. Ait Sidhoum, M.; El Kaïm, L.; Grimaud, L. Tetrahedron 2018acceptedDOI: 10.1016/j.tet.2018.04.058

 

105. Coupling electrochemistry and TIRF-microscopy with the fluorescent false neurotransmitter FFN102 supports the fluorescence signals during single vesicle exocytosis detection. Liu, X.; Hu, L.; Pan, N.; Grimaud, L.; Labbé, E. ; Buriez, O.; Delacotte, J.; Lemaître, F.; Guille-Collignon, M. Biophys. Chem. 2018235, 48-55.DOI: 10.1021/acs.bioconjchem.7b00825

 

104. Labelling of hyaluronic acids with a Re-tricarbonyl tag and percutaneous penetration into human skin studied by multimodal imaging. Henry, L.; Delsuc, N.; Laugel, C.; Lambert, F.; Sandt, C.; Hostachy, S.; Bernard, A. S.; Bertrand, H. C.; Grimaud, L.; Baillet-Guffroy, A.; Policar, C. Bioconjugate Chem. 2018, 29, 987-991.

 

103. Evidence for a Cooperative Mechanism Involving two Palladium(0) Centers in the Oxidative Addition of Iodoarenes. Perego, L. A.; Payard, P. A.; Haddou, B.; Ciofini, I.; Grimaud, L. Chem. Eur. J. 201824, 2192-2199. DOI: 10.1002/chem.201704899

 

102. TiCl4-mediated synthesis of 3,4-hetero-disubstituted isocoumarins by means of isocyanide insertion reactions. Ponra, S.; Nyadanu, A.; Maurin, S.; El Kaïm, L.; Grimaud, L.; Vitale, M. R. Synthesis201850, 1331–1342DOI: 10.1055/s-0036-1591733

 

2017

101. Copper-Catalyzed Hydroamination of N-Allenylazoles: Access to Amino-Substituted N-Vinylazoles. Perego, L. A.; Blieck, R.; Michel, J.; Ciofini, I.; Grimaud, L.; Taillefer, M.; Monnier, F. Adv. Synth. Cat. 2017359, 4388–4392. DOI: 10.1002/adsc.201700965

 

100. Copper-Catalyzed Hydroamination of Allenes: from Mechanistic Understanding to Methodology Development. Perego, L. A.; Blieck, R.; Groué, A.; Monnier, F.; Taillefer, M.; Ciofini, I.; Grimaud, L. ACS Catal20177, 4253−4264. DOI: 10.1021/acscatal.7b00911

 

99. Stereoselective access to trisubstituted fluorinated alkenyl thioethers. Fabre, I.; Poisson, T.; Pannecoucke, X.; Gillaizeau, I.; Ciofini, I.; Grimaud, L. Catal. Sci. Technol. 20177, 1921-1927.DOI10.1039/C7CY00076F

 

98. N-N bond formation in Ugi Processes: from nitric acid to libraries of Nitramines. Mercalli, V.; Nyadanu, A.; Cordier, C.; Tron, G. C.; Grimaud, L.; El Kaim, L. Chem. Comm. 201753, 2118-2121.DOI10.1039/C6CC10288C

 

97. A dual functional electroactive and fluorescent probe for coupled measurements of vesicular exocytosis with high spatial and temporal resolution. Liu, X.; Savy, A.; Maurin, S.; Grimaud, L.; Labbé, E.; Buriez, O.; Delacotte, J.; Amatore, C.; Lemaître, F.; Guille-Collignon, M. Angew. Chem. Int. Ed. 2017, 2366-2370.

 

96. Ugi-Smiles couplings of purine derivatives. Ben Abdessalem, A.; Abderrahim, R.; Dos Santos, A.; El Kaïm, L.; Grimaud, L. Synlett 201728, 691–694. DOI 10.1055/s-0036-1588117

 

2016

95. Review: Role of Fluoride Ions in Palladium-Catalyzed Cross-Coupling Reactions. Jutand, A.; Grimaud, L. Synthesis 201649, 1182-1189.

 

94. Benzoxazinone syntheses through Passerini-Smiles couplings. Martinand-Lurin, E.; Dos Santos, A.; Robineau, E.; Retailleau, P.; Dauban, P.; Grimaud, L.; El Kaïm, L. Molecules 201616, 1257-1270. DOI: 10.1016/j.tetlet.2014.07.088

 

93. TiCl4-Mediated Preparation of Thiophtalide Derivatives via Formal Thio-Passerini Reactions. Ponra, S.; Nyadanu, A.; El Kaïm, L.; Grimaud, L.; Vitale, M. R. Org. Lett. 201618, 4060–4063. DOI: 10.1021/acs.orglett.6b01937

 

92. Multiple Roles of Isocyanides in Imidoylative Palladium-Catalyzed Couplings - A Mechanistic Study. Perego, L. A.; Fleurat-Lessard, P.; El Kaïm, L.; Ciofini, I.; Grimaud, L. Chem. Eur J. 201622, 15491-15500. DOI: 10.1002/chem.201602913

 

91. Antagonist Effect of Acetates in C-N bond formation with in situ generated diazonium salts: a combined theoretical and experimental study. Fabre, I.; Perego, L. A.; Bergès, J.; Ciofini, I.; Grimaud, L.; Taillefer, M. Eur J. Org. Chem. 2016, 5887–5896DOI: 10.1002/ejoc.201600891

 

90. Mechanistic Studies on the Pd-Catalyzed Direct C5 Arylation of Imidazoles: the Fundamental Role of the Azole as a Ligand for Pd. Perego, L. A.; Grimaud, L.; Bellina, F. Adv. Synth. Cat. 2016358, 597-609. DOI: 10.1002/adsc.201500888

 

2015

89. Hypervalent iodine-mediated synthesis of 1,2-dispirodienones: experimental and theoretical investigations. Hromjakova, T.; Retailleau, P.; Grimaud, L.; Gandon, V.; Chabaud, L.; Guillou, C. Eur. J. Org. Chem. 2015, 7494-7503.

 

88. Transition-Metal-Free alpha-Arylation of Enolizable Aryl Ketones and Mechanistic Evidence for a Radical Process. Pichette-Drapeau, M.; Fabre, I.; Grimaud, L.; Ciofini, I.; Ollevier, T.; Taillefer, M. Angew. Chem. Int. Ed. 201554, 10587-10591DOI: 10.1002/anie.201502332

 

2014

87. Review: The Ugi-Smiles and Passerini-Smiles couplings: a story about phenols in Isocyanide based Multicomponent Reactions El Kaïm, L.; Grimaud, L. Eur. J. Org. Chem. 2014, 7749–7762.

 

86. Benzoxazinone synthesis via Passerini-Smiles couplings. Martinand-Lurin, E.; El Kaïm, L.; Grimaud, L. Tetrahedron Lett. 201455, 5144-5146.

 

85. Kinetic Data on the Synergetic Role of Amines and Water in the Reduction of Phosphine Ligated-Palladium(II) to Palladium(0). Amatore, C.; El Kaïm, L.; Grimaud, L.; Jutand, A.; Meigné, A.; Romanov, G., Eur. J.O.C 2014, 4709-4713. DOI : 10.1002/ejoc.201402519

 

84. Three Roles for Fluoride Ions in Palladium-Catalyzed Hiyama Reactions: Transmetallation of ArPdFL2 by Ar’Si(OR)3. Amatore, C.; Grimaud, L.; Le Duc, G.; Jutand, A, Angew. Chem. Int. Ed. 201453, 6982–6985. DOI: 10.1002/anie.201400956

 

83. Copper-Catalyzed Olefinic C-H Difluoroacetylation of Enamides. Caillot, G.; Dufour, J.; Belhomme, M. C.; Poisson, T.; Grimaud, L.; Pannecoucke, X.; Gillaizeau, I. Chem. Commun. 201450, 5887-5890.

 

82. Nitrile synthesis through catalyzed cascades involving acid-nitrile exchange reaction. Cartigny,D.; El Kaïm, L.; Grimaud, L.; Marion, P; Jacquot, R. Synthesis 201446, 1802-1806.

 

81. Double Smiles rearrangement of Passerini adducts towards benzoxazinones. Martinand-Lurin, E.; Dos Santos, A.; El Kaïm, L.; Grimaud, L.; Retailleau, P. Chem. Comm. 201450, 2214-2217.DOI: 10.1039/C3CC49022J

 

2013

80. Pyrrolo[2,3-d]pyrimidine synthesis through activation of N-benzyl groups by distal amides. El Kaïm, L.; Grimaud, L.; Wagschal, S. Org. Biomol. Chem. 201311, 6883-6885.

 

79. Substituent Effects in Ugi-Smiles Reactions. Chéron, N.; Ramozzi, R.; El Kaïm, L.; Grimaud, L.; Fleurat-Lessard, P. J. Phys. Chem. A 2013, 117, 8035−8042.

 

78. Lewis acid mediated fragmentation of tetrazoles towards triazoles. El Kaïm, L.; Grimaud, L.; Pravin, P. Eur. J. Org. Chem 201322, 4752–4755.

 

77. Three-Component Metal-Free Arylation of Isocyanides. Basavanag, U. M. V.; Dos Santos, A.; El Kaïm, L.; Gamez-Montano, R.; Grimaud, L. Angew. Chem. Int. Ed. 201352, 7194-7197. DOI: 10.1002/anie.201302659

 

76. Metal-free aerobic oxidation of benzazole derivatives. Dos Santos, A.; El Kaïm, L. ; Grimaud, L. Org. Biomol. Chem. 201311, 3282-3287.

 

2012

75. Oxazole synthesis from isocyanides. El Kaïm, L.; Grimaud, L.; Pravin, P. Synlett 2012, 1361-1363.

 

74. Palladium catalyzed ring-opening of aminocyclopropyl Ugi adducts. Dos Santos, A.; El Kaïm, L.; Grimaud, L.; Ramozzi, R. Synlett 2012, 438-442.

 

73. Four-component synthesis of indazole through Ugi-azide coupling. El Kaïm, L.; Grimaud, L.; Purumandla, S. R. Synlett 2012, 295-297.

 

72. Challenging 50 years of established views on Ugi reaction: a theoretical approach. Chéron, N.; Ramozzi, R.; El Kaïm, L.; Grimaud, L.; Fleurat-Lessard, P. J. Org. Chem. 201277, 1361–1366.

 

71. Ugi-Smiles coupling of thiouracil derivatives towards 2,4-diamino pyrimidines. Ait Sidhoum, M.; El Kaïm, L. ; Grimaud, L. Synlett 2012, 632-636.

 

70. Ugi-Smiles couplings of 4-substituted pyridine derivatives: a fast access to chloroquine analogues. El Kaïm, L.; Grimaud, L.; Pravin, P. Org. Lett. 201214, 476-478.

 

2011

69. Xanthate Based Radical Cascade Toward Multicomponent Formation of Pyrrolopyrimidines. El Kaïm, L.; Grimaud, L.; Pravin, P. Molecules 2011, 16, 9261-9273.

 

68. Copper-triggered oxidative cascade as Ugi post-condensation towards pyrazoles. El Kaïm, L.; Grimaud, L.; Ronsseray, C. Beilstein J. Chem. 20117, 1310-1314.

 

67.Straightforward four-component access to spiroindolines. El Kaïm, L.; Grimaud, L.; Le Goff, X. –F.; Menes-Arzate, M.; Miranda, L. D. Chem. Commun. 201147, 8145-8147. DOI:
10.1039/C1CC12236C

 

66. Evidences for the Key-Role of Hydrogen Bonds in SNAr. Chéron, N.;El Kaïm, L.; Grimaud, L.; Fleurat-Lessard, P.  Chem. Eur. J. 201117, 14929–14934.

 

65. A Density Functional Theory Study of the Nef-Isocyanide Reaction: Mechanism, Influence of Parameters and Scope. Chéron, N. ; El Kaïm, L. ; Grimaud, L. ; Fleurat-Lessard, P. J. Phys. Chem. A2011, 115, 10106-10112.

 

64. Phosphite mediated synthesis of benzimidazoles: a one-pot four-component approach from nitrophenols. El Kaïm, L.; Grimaud, L. ; Purumandla, S. P. Eur. J. Org. Chem. 201131, 6177–6180.

 

63. Three-component strategy towards 5-membered heterocycles from isocyanide dibromides. El Kaïm, L.; Grimaud, L.; Pravin, P. Org. Lett. 201113, 1261–1263. DOI: 10.1021/ol200003u

 

62. Copper catalyzed aerobic oxidative cyclization of hydrazones to pyrazolinones. Dos Santos, A.; El Kaïm, L.; Grimaud, L.; Ronsseray, C. Eur. J. Org. Chem. 2011, 3117–3121.

 

61. Allyl and Benzyl Dance under Basic Conditions. El Kaïm, L.; Grimaud, L.; Purumandla, S. R. Synlett 2011, 1816-1820.

 

60Multicomponent Synthesis of Fused Benzimidazolopiperazines. El Kaïm, L.; Grimaud, L.; Purumandla, S. P. J. Org. Chem. 201176, 4728-4733.

 

59.  A new multicomponent reaction for the synthesis of pyridines via cycloaddition of azadienes and ketenimines. Coffinier, D.; El Kaïm, L.; Grimaud, L.; Ruijter, E.; Orru, R. V. A. Tetrahedron Lett. 201152, 3023-3025.

 

58. Palladium catalyzed ring opening of furans as a route to a,b-unsaturated aldehydes. El Kaïm, L.; Grimaud, L.; Wagschal, S. Chem. Comm. 2011, 47, 1887-1889DOI: 10.1039/C0CC04164E

 

57. Smiles cascades towards heterocyclic scaffolds. El Kaïm, L.; Le Goff, X. -F.; Grimaud, L.; Schiltz, A. Org. Lett. 201113, 534-536. DOI: 10.1021/ol1028817

 

2010

56. Review: Ugi–Smiles couplings: new entries to N-aryl carboxamide Derivatives. El Kaïm, L. ; Grimaud, L. Mol. Div. 201014, 855-867.

 

55. New pyridine synthesis from hydrazone. Coffinier, D.; El Kaïm, L.; Grimaud, L.; Hadrot, S.  Tetrahedron Lett. 201051, 6186-6188.

 

54. Ammonia in Ugi-Smiles couplings. Barthelon, A.; El Kaïm, L.; Gizzi, M.; Grimaud, L. Synlett 2010, 2784-2788.

 

53. Ugi-Smiles reactions in water. El Kaïm, L.; Grimaud, L.; Purumandla, S. R. Tetrahedron Lett. 201051, 4962-4964.

 

52. Three-Component Fischer Indole Synthesis. El Kaïm, L.; Grimaud, L.; Ronsseray, C. Synlett 2010, 2296-2298.

 

51. Nef/Perkow access to indolizine derivatives. Coffinier, D.; El Kaïm, L. ; Grimaud, L. Synlett 2010, 2474-2476.

 

50. 1,2,4-Triazole synthesis via amidrazones. El Kaïm, L.; Gizzi, M.; Grimaud, L. Synlett 2010, 1771-1774.

 

49. Towards new pyrrolo[2,3-d]pyrimidines scaffolds. El Kaïm, L.; Grimaud, L.; Wagschal, S.  J. Org. Chem. 201075, 5343–5346. DOI: 10.1021/jo100759b

 

48. New xanthate-based radical cyclization onto alkynes. El Kaïm, L.; Grimaud, L.; Miranda, L. D.; Vieu, E.; Cano-Herrera, M. A.; Perez-Labrada, K. Chem. Commun. 201046, 2489 – 2491.

 

47. Four-component Synthesis of Imidazolinium-fused Heterocycles from Ugi-Smiles Couplings. Barthelon, A.; Legoff, X.-F.; El Kaïm, L.; Grimaud, L. Synlett 2010, 153-157.

 

2009

46. Review: Beyond the Ugi reaction: less conventional interactions between isocyanides and iminium species (sur invitation du Pr W. B. Motherwell). El Kaïm, L.; Grimaud, L. Tetrahedron 200965, 2153-2171.

 

45. Isocyanide-based multicomponent reaction ‘without’ isocyanides. El Kaïm, L.; Grimaud, L.; Schiltz, A. Synlett 2009, 1401-1404.

 

44. One-pot synthesis of oxazoles using isocyanide surrogates. El Kaïm, L.; Grimaud, L.; Schiltz. A. Tetrahedron Lett. 200950, 5235-5237.

 

43. Unconventional oxazole formation from isocyanides. Dos Santos, A.; El Kaïm, L.; Grimaud, L.; Ronsseray, C. Chem. Commun. 2009, 3907-3909.

 

42. Isocyanide-free Ugi reactions. El Kaïm, L.; Grimaud, L.; Schiltz, A. Org. Biomol. Chem. 20097, 3024-3026.

 

41. Three-component Nef/Huisgen access to 1,2,4-triazoles. El Kaïm, L.; Grimaud, L.; Wagschal, S. Synlett 2009, 1315-1317.

 

40. Isocyanide-Based Two-Step Three-Component Keteneimine Formation. Coffinier, D.; El Kaïm, L.; Grimaud, L. Org. Lett. 200911, 1825-1827.DOI: 10.1021/ol9004432

 

39. Three component Ugi-Smiles couplings of cyclic imines. El Kaïm, L.; Grimaud, L.; Oble, J. Wagschal, S. Tetrahedron Lett. 200950, 1741-1743.

 

38. New benzotriazole and benzimidazole scaffolds from Ugi-Smiles couplings of isocyanides. Coffinier, D.; El Kaïm, L.; Grimaud, L. Org. Lett. 200911, 995-997. DOI: 10.1021/ol8029438

 

2008

37. Thiols in Ugi- and Passerini-Smiles-type couplings. Barthelon, A.; El Kaïm, L.; Gizolme, M.; Grimaud, L. European J. Org. Chem. 2008, 35, 5974-5987. DOI: 10.1002/ejoc.200800859

 

36. New MCR-Heck-Isomerization Cascade toward Indoles. El Kaïm, L.; Gizzi, M.; Grimaud, L. Org. Lett200810; 3417-3419. DOI: 10.1021/ol801217a

 

35. Intramolecular Kulinkovitch-de Mejeire reactions of various disubstituted alkenes bearing amide groups. Madelaine, C.; Ouhamou, N.; Chiaroni, A.; Vedrenne, E.; Grimaud, L.; Six, Y. Tetrahedron 2008 64, 8878-8898.

 

34. Ugi-Smiles access to pyrazine scaffolds. Barthelon, A.; Dos Santos, A.; El Kaïm, L.; Grimaud, L. Tetrahedron Lett 200849, 3208-3211.

 

33. Isocyanide addition to acylphosphonates: A formal Passerini reaction of acyl chlorides. Coffinier, D.; El Kaïm, L.; Grimaud, L. Synlett 2008, 1133-1136

 

32. New Pd catalyzed aerobic oxidative cleavage and cyclization of N-aryl peptid derivatives. El Kaïm, L.; Grimaud, L.; Ibarra, T.; Montano-Gamez, R. Chem. Comm. 200811, 1350-1352. DOI: 10.1039/B716849G

 

2007

31. From simple Ugi adducts to indanes and amidomalonates: new manganese (III) induced radical cascades. El Kaïm, L.; Grimaud, L.; Vieu, E. Org. Lett., 20079, 4171-4173. DOI: 10.1021/ol701678d

 

30. Ugi-Smiles access to quinoxaline derivatives. Oble, J.; El Kaïm, L.; Gizzi, M.; Grimaud, L. Heterocycles200773, 503-517.

 

29. New Ugi-Smiles-metathesis strategy towards the synthesis of pyrimido azepines. El Kaïm, L.; Gizolme, M.; Grimaud, L.; Oble, J. J. Org. Chem200772, 5835-5838. DOI: 10.1021/jo070706c

 

28. Smiles rearrangements in Ugi and Passerini type couplings: new multicomponent accesses to O- and N‑aryl amides. El Kaïm, L.; Gizolme, M.; Grimaud, L.; Oble, J. J. Org. Chem200772, 4169-4180. DOI: 10.1021/jo070202e

 

27. New benzothiazole and benzoxazole scaffolds from the Ugi–Smiles couplings of heterocyclic thiols. El Kaïm, L.; Gizolme, M.; Grimaud, L.; Oble, J. Synlett 2007, 465-469.

 

26. New Ugi/Pictet–Spengler multicomponent formation of polycyclic diketopiperazines from isocyanides and α-keto acids. El Kaïm, L. ; Gageat, M.; Gaultier, L.; Grimaud, L. Synlett 2007, 500-502.

 

25. New indolizines template from the Ugi reaction. El Kaïm, L.; Gizolme, M.; Grimaud, L. Synlett 2007, 227-230.

 

2006

24O-Arylative Passerini reactions. El Kaïm, L.; Gizolme, M.; Grimaud, L. Org. Lett. 2006, 8, 5021-5023. DOI: 10.1021/ol0617502

 

23. Direct access to heterocyclic scaffolds by new multicomponent Ugi-Smiles couplings. El Kaïm, L.; Gizolme, M.; Grimaud, L.; Oble, J. Org. Lett. 2006, 8, 4019-4021. DOI: 10.1021/ol061605o

 

22. Ugi /xanthate cyclizations as a radical route to lactam scaffolds. El Kaïm, L.; Grimaud, L.; Miranda, L.; Vieu, E. Tetrahedron Lett. 2006, 47, 8259-8261.

 

21. New ortho-quinone methide formation: application to three component coupling of isocyanide, aldehyde and phenol. El Kaïm, L.; Grimaud, L.; Oble, J. Organic Biomol. Chem. 20064, 3410-3413.

 

20. Solvent-free preparation of amidophosphonates from isocyanides. El Kaïm, L.; Grimaud, L.; Hadrot, S. Tetrahedron Lett. 2006, 47, 3945-3947.

 

2005

19. Phenol Ugi-Smiles systems: Strategies for the multicomponent of N-arylation of primary amines with isocyanides, aldehydes and phenols. El Kaïm, L.; Grimaud, L.; Oble, J. Angew. Chem. Int. Ed. 200544, 7961-7964. DOI: 10.1002/anie.200502636

 

18. Towards the Synthesis of Paulitin: New Insights into Enyne-Metathesis Mechanism. Vedrenne, E.; Royer, F.; Oble, J.; El Kaïm, L.; Grimaud, L. Synlett 200515, 2379-2381.

 

17. Formation of new phosphates from aldehydes by a DBU-catalysed phospha-Brook rearrangement in a polar solvent. El Kaïm, L.; Gaultier, L.; Grimaud, L.; Dos Santos, A. Synlett 200515, 2335-2336.

 

16. Dramatic effect of boron-based Lewis acid in cross-metathesis reactions. Vedrenne, E.; Dupont, H.; Oualef, S.; El Kaïm, L.; Grimaud, L. Synlett 20054, 670-672.

 

2004

15. New access to fluorinated ketoglycolic acid derivatives from trifluoropyruvamides. Colin, T.; El Kaïm, L.; Gaultier, L.; Grimaud, L.; Gatay, L. Tetrahedron Lett200445, 5611-5613.

 

14. From isocyanides to trichloropyruvamides : Application to new preparation of Oxamide derivatives. El Kaïm, L.; Gaultier, L.; Grimaud, L.; Vieu, E. Tetrahedron Lett. 200445, 8047-8048.

 

13. First Carbamates Conversion to Amides by Simple Alkyl Group Transfer from Trialkylalanes. El Kaïm, L.; Grimaud, L.; Perroux, Y.; Tirla, C. Org. Lett. 2004, 6, 381-383.

 

12. Condensation of ɤ-hydroxy sulfones and vinyl sulfones with aldehydes and ketones using phenyllithium as base. Rotulo-Sims, D.; Grimaud, L.; Prunet, J. Comptes Rendus, 2004, 941-944.

 

2003

11. New insight into the azaenamine behavior of N-Arylhydrazones: first Aldol and improved Mannich reactions with unactivated aldehydes. El Kaïm, L.; Gautier, L.; Grimaud, L.; Michaut, V. Synlett200312, 1844-1846.

 

10. The Mannich Reaction of Hydrazones: Improved Reactivity under Solvent-free Conditions. El Kaïm, L.; Gautier, L.; Grimaud, L.; M. Harwood, L.; Michaut, V. Green Chem. 20035, 477-479.

 

9. New trimethylaluminum induced Mannich type reaction of hydrazones. El Kaïm, L.; Grimaud, L.; Perroux, Y.; Tirla, C. J. Org. Chem. 200368, 8733-8735.

 

8. Selective Domino Ring-Closing Metathesis-Cross-Metathesis Reactions between Enynes and Electron-deficient Alkenes. Royer, F.; Vilain, C.; El Kaïm, L; Grimaud, L. Org. Lett. 20035, 2007-2009.

 

2002

7. Diastereoselective Synthesis of Protected syn 1,3-Diols: Preparation of the C16-C24 Portion of Dolabelides. Grimaud, L.; de Mesmay, R.; Prunet, J. Org. Lett. 2002; 4; 419-421.  

 

6. Amines addition to a-nitrohydrazones: application to amidrazones and triazoles formation. El Kaïm, L.; Grimaud, L.; Jana, N. K.; Mettetal, F.; Tirla, C. Tetrahedron Lett. 2002, 43, 8925-8927.

 

5. Studies towards the synthesis of Fipronil analogues: improved decarboxylation of a-hydrazonoacid derivatives. Ancel, J. E.; El Kaïm, L.; Gadras, A.; Grimaud, L.; Jana, N. K. Tetrahedron Lett. 200243, 8319-8321.

 

4. Synthesis of protected syn 1,3-diols by intramolecular conjugate addition to vinyl sulfones. Grimaud, L.; Rotulo, D., Ros-Perez, R.; Guitry-Azam, L.; Prunet, J. Tetrahedron Lett. 200243, 7477-7479.

 

3. a-Nitrohydrazones: versatile intermediates for phosphonate derivatives formation from primary nitro compounds. El Kaïm, L.; Grimaud, L.; Jana, N. K.; Tirla, C. Tetrahedron Lett. 2002, 43, 2037-2038.

 

2. The Mannich reaction of hydrazones amenable to solid phase synthesis: a powerful tool for heterocycle preparation. Atlan, V.; El Kaïm, L.; Grimaud, L.; Jana, N. K.; Majee, A. Synlett 20022, 352-354.

 

1. Diastereoselective intramolecular Diels-Alder reactions towards the synthesis of a taxol C-ring precursor. Grimaud, L.; Férézou, J.-P.; Prunet, J.; Lallemand, J. –Y. Tetrahedron 1997, 53, 9253-9268.

 

 


Chapters in collective international books

 

- Smiles rearrangement. Molecular Rearrangements in Organic Synthesis. El Kaïm, L.; Grimaud, L. Editor: Rojas, C. M., Wiley: 2015.

 

 

- Ugi-Smiles and Passerini-Smiles couplings. Multicomponent Reactions in Organic Synthesis. El Kaïm, L.; Grimaud, L. Editors : Zhu, J.; Wang, Q.; Wang, M.-X. Wiley: 2015.

 

- Ugi and Passerini Reactions with Carboxylic Acid Surrogates. Isocyanide Chemistry: Applications in Synthesis and Material Science. El Kaïm, L.; Grimaud, L. Editor : Nenadjenko, V. Wiley: 2012.

 

- Cross-Metathesis in Natural Products Synthesis. Prunet, J.; Grimaud, L. Editors : J. Cossy, S. Arseniyadis, C. Meyer, Wiley: 2010.

 

- One or More C=C Bond(s) Formed by Condensation: Condensation of Nonheteroatom Linked Functions, Halides, Chalcogen or Nitrogen Functions. Prunet, J.; Grimaud, L. Chapitre 1.15 du Comprehensive Organic Functional Group Transformations, 2e édition, editors: A. R. Katritzky et R. J. K. Taylor, Elsevier: 2005.