Synthesis 2014; 46(23): 3229-3232
DOI: 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
Further Information

Publication History

Received: 19 May 2014

Accepted after revision: 18 July 2014

Publication Date:
27 August 2014 (online)


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.

 
  • 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