Mild and Metal-Free Diastereoselective Synthesis of N-tert-Butanesulfinylamines by Using Tetrakis(dimethylamino)ethylene

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

sulfinimines - diastereoselectivity - amines - metal-free - chiral auxiliary

• 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