Synthesis, Table of Contents Synthesis 2014; 46(23): 3229-3232DOI: 10.1055/s-0034-1378636 paper © Georg Thieme Verlag Stuttgart · New York Mild and Metal-Free Diastereoselective Synthesis of N-tert-Butanesulfinylamines by Using Tetrakis(dimethylamino)ethylene Cédric Spitz Aix-Marseille Université, CNRS, ICR UMR 7273, Equipe Pharmaco-Chimie Radicalaire, Faculté de Pharmacie, 27 Boulevard Jean Moulin – CS 30064 – 13385 Marseille Cedex 05, France Fax: +33(4)91794677 Email: patrice.vanelle@univ-amu.fr , Anna Lin Aix-Marseille Université, CNRS, ICR UMR 7273, Equipe Pharmaco-Chimie Radicalaire, Faculté de Pharmacie, 27 Boulevard Jean Moulin – CS 30064 – 13385 Marseille Cedex 05, France Fax: +33(4)91794677 Email: patrice.vanelle@univ-amu.fr , Thierry Terme Aix-Marseille Université, CNRS, ICR UMR 7273, Equipe Pharmaco-Chimie Radicalaire, Faculté de Pharmacie, 27 Boulevard Jean Moulin – CS 30064 – 13385 Marseille Cedex 05, France Fax: +33(4)91794677 Email: patrice.vanelle@univ-amu.fr , Patrice Vanelle* Aix-Marseille Université, CNRS, ICR UMR 7273, Equipe Pharmaco-Chimie Radicalaire, Faculté de Pharmacie, 27 Boulevard Jean Moulin – CS 30064 – 13385 Marseille Cedex 05, France Fax: +33(4)91794677 Email: patrice.vanelle@univ-amu.fr › Author Affiliations Recommend Article Abstract Buy Article All articles of this category Abstract A mild and metal-free diastereoselective synthesis of N-tert-butanesulfinylamines was developed by using a strategy based on tetrakis(dimethylamino)ethylene. Good yields and diastereoselectivities were achieved by addition of o-nitrobenzyl chloride or 4-[4-(chloromethyl)phenyl]-1,2-dimethyl-5-nitro-1H-imidazole to readily available N-tert-butanesulfinimines. Key words Key wordssulfinimines - diastereoselectivity - amines - metal-free - chiral auxiliary Full Text References References 1 Hili R, Yudin AK. Nat. Chem. Biol. 2006; 2: 284 2 Robak MT, Herbage MA, Ellman JA. Chem. Rev. 2010; 110: 3600 3 Buesking AW, Baguley TD, Ellman JA. Org. Lett. 2011; 13: 964 4 Sapountzis I, Dube H, Lewis R, Gommermann N, Knochel P. J. Org. Chem. 2005; 70: 2445 5a Takechi N, Aït-Mohand S, Médebielle M, Dolbier WR. Jr. Tetrahedron Lett. 2002; 43: 4317 5b Pooput C, Médebielle M, Dolbier WR. Jr. Org. Lett. 2004; 6: 301 5c Pooput C, Médebielle M, Dolbier WR. Jr. J. Org. Chem. 2006; 71: 3564 6a Montana M, Terme T, Vanelle P. Tetrahedron Lett. 2005; 46: 8373 6b Amiri-Attou O, Terme T, Vanelle P. Molecules 2005; 10: 545 6c Montana M, Terme T, Vanelle P. Tetrahedron Lett. 2006; 47: 6573 6d Juspin T, Terme T, Vanelle P. Synlett 2009; 1485 6e Nadji-Boukrouche AR, Khoumeri O, Terme T, Liacha M, Vanelle P. ARKIVOC 2010; (x): 358 6f Montana M, Terme T, Vanelle P. Lett. Org. Chem. 2010; 7: 453 6g Juspin T, Giuglio-Tonolo G, Terme T, Vanelle P. Synthesis 2010; 844 7 Spitz C, Khoumeri O, Terme T, Vanelle P. Synlett 2013; 24: 1725 8a Crozet MP, Archaimbault G, Vanelle P, Nouguier R. Tetrahedron Lett. 1985; 26: 5133 8b Curti C, Laget M, Ortiz Carle A, Gellis A, Vanelle P. Eur. J. Med. Chem. 2007; 42: 880 8c Cohen A, Crozet MD, Rathelot P, Vanelle P. Green Chem. 2009; 11: 1736 8d Verhaeghe P, Azas N, Hutter S, Castera-Ducros C, Laget M, Dumètre A, Gasquet M, Reboul J.-P, Rault S, Rathelot P, Vanelle P. Bioorg. Med. Chem. 2009; 17: 4313 9a Jorgensen MA, Manos J, Mendz GL, Hazell SL. J. Antimicrob. Chemother. 1998; 41: 67 9b Upcroft JA, Campbell RW, Benakli K, Upcroft P, Vanelle P. Antimicrob. Agents Chemother. 1999; 43: 73 9c Citron DM, Tyrrell KL, Warren YA, Fernandez H, Merriam CV, Goldstein EJ. C. Anaerobe 2005; 11: 315 9d Leitsch D, Kolarich D, Wilson IB. H, Altmann F, Duchêne M. PLoS Biol. 2007; 5: e211 9e Crozet MD, Botta C, Gasquet M, Curti C, Rémusat V, Hutter S, Chapelle O, Azas N, De Méo M, Vanelle P. Eur. J. Med. Chem. 2009; 44: 653 9f Kim P, Kang S, Boshoff HI, Jiricek J, Collins M, Singh R, Manjunatha UH, Niyomrattanakit P, Zhang L, Goodwin M, Dick T, Keller TH, Dowd CS, Barry III CE. J. Med. Chem. 2009; 52: 1329 9g Dunn LA, Burgess AG, Krauer KG, Eckmann L, Vanelle P, Crozet MD, Gillin FD, Upcroft P, Upcroft JA. Int. J. Antimicrob. Agents 2010; 36: 37
