A facile method for the N-alkylated of α-amino esters

Tetrahedron

Volumn 53, Issue 46, 1997, Pages 15787-15798

  Bowman, W Russell ^a   Coghlan, Daniel R ^a  

^a LOUGHBOROUGH UNIVERSITY   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID DERIVATIVE; SULFONAMIDE;

ALKYLATION; ARTICLE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; REACTION ANALYSIS;

EID: 0030869889     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)10015-1     Document Type: Article

References (26)

1. Bowman, W.R.; Broadhurst, M. J.; Coghlan, D.R.; Lewis, K.A. Tetrahedron Lett., 1997, 38, in print.
2. Adlington, R.M.; Mantell, S.J. Tetrahedron, 1992, 48, 6529-6536.
3. Fukuyama, T.; Jow, C.-K.; Cheung, M. Tetrahedron Lett., 1995, 36, 6373-6374.
4. Bhatt, U.; Mohamed, N.; Just, G. Tetrahedron Lett., 1997, 38, 3679-3682.
5. Mitsunobu, O. In Comprehensive Organic Synthesis, Trost, B.M.; Fleming, I. Eds.; Pergamon Press: Oxford, 1991, vol. 6, pp. 65-101.
6. Some useful examples: Borch, R.F.; Bernstein, M.D.; Durst, H.D. J. Am. Chem. Soc., 1971, 93, 2897-2904; Hardegger, von E.; Szabo, F.; Liechti, P.; Rostetter, Ch.; Zankowska-Jasinska, W. Helv. Chim. Acta, 1968, 51, 78-85; Baker, J.K.; Little, T.L. J. Med. Chem., 1985, 28, 46-50; Boger, D.L.; Zhou, J. J. Am. Chem. Soc., 1993, 115, 11426-11433; Cheeseright, T.J.; Edwards, A.J.; Elmore, D.T.; Jones, J.H.; Raissi, M.; Lewis, E.C. J. Chem. Soc. Perkin Trans. 1, 1994, 1595-1600.
7. Some useful examples: Borch, R.F.; Bernstein, M.D.; Durst, H.D. J. Am. Chem. Soc., 1971, 93, 2897-2904; Hardegger, von E.; Szabo, F.; Liechti, P.; Rostetter, Ch.; Zankowska-Jasinska, W. Helv. Chim. Acta, 1968, 51, 78-85; Baker, J.K.; Little, T.L. J. Med. Chem., 1985, 28, 46-50; Boger, D.L.; Zhou, J. J. Am. Chem. Soc., 1993, 115, 11426-11433; Cheeseright, T.J.; Edwards, A.J.; Elmore, D.T.; Jones, J.H.; Raissi, M.; Lewis, E.C. J. Chem. Soc. Perkin Trans. 1, 1994, 1595-1600.
8. Some useful examples: Borch, R.F.; Bernstein, M.D.; Durst, H.D. J. Am. Chem. Soc., 1971, 93, 2897-2904; Hardegger, von E.; Szabo, F.; Liechti, P.; Rostetter, Ch.; Zankowska-Jasinska, W. Helv. Chim. Acta, 1968, 51, 78-85; Baker, J.K.; Little, T.L. J. Med. Chem., 1985, 28, 46-50; Boger, D.L.; Zhou, J. J. Am. Chem. Soc., 1993, 115, 11426-11433; Cheeseright, T.J.; Edwards, A.J.; Elmore, D.T.; Jones, J.H.; Raissi, M.; Lewis, E.C. J. Chem. Soc. Perkin Trans. 1, 1994, 1595-1600.
9. Some useful examples: Borch, R.F.; Bernstein, M.D.; Durst, H.D. J. Am. Chem. Soc., 1971, 93, 2897-2904; Hardegger, von E.; Szabo, F.; Liechti, P.; Rostetter, Ch.; Zankowska-Jasinska, W. Helv. Chim. Acta, 1968, 51, 78-85; Baker, J.K.; Little, T.L. J. Med. Chem., 1985, 28, 46-50; Boger, D.L.; Zhou, J. J. Am. Chem. Soc., 1993, 115, 11426-11433; Cheeseright, T.J.; Edwards, A.J.; Elmore, D.T.; Jones, J.H.; Raissi, M.; Lewis, E.C. J. Chem. Soc. Perkin Trans. 1, 1994, 1595-1600.
10. Some useful examples: Borch, R.F.; Bernstein, M.D.; Durst, H.D. J. Am. Chem. Soc., 1971, 93, 2897-2904; Hardegger, von E.; Szabo, F.; Liechti, P.; Rostetter, Ch.; Zankowska-Jasinska, W. Helv. Chim. Acta, 1968, 51, 78-85; Baker, J.K.; Little, T.L. J. Med. Chem., 1985, 28, 46-50; Boger, D.L.; Zhou, J. J. Am. Chem. Soc., 1993, 115, 11426-11433; Cheeseright, T.J.; Edwards, A.J.; Elmore, D.T.; Jones, J.H.; Raissi, M.; Lewis, E.C. J. Chem. Soc. Perkin Trans. 1, 1994, 1595-1600.
11. Ohfune, Y.; Kurokawa, N.; Higuchi, N.; Saito, M.; Hashimoto, M.; Tanaka, T. Chem. Lett., 1984, 441-444.
12. Ando, A.; Shioiri, T. Tetrahedron, 1989, 45, 4969-4988.
13. Whitesell, J. K. In Comprehensive Organic Synthesis, Trost, B.M.; Fleming, I. Eds.; Pergamon Press: Oxford, 1991, vol. 6, pp. 703-732.
14. Bruncko, M.; Khuong, T.A.V.; Sharpless, K.B. Angew. Chem., Int. Ed. Eng., 1996, 35, 454-456; Li, G.C.; Chang, M.T.; Sharpless, K.B. Angew. Chem. Int. Ed. Eng., 1996, 35, 451-454; Reiser, O. Angew. Chem. Int. Ed. Eng., 1996, 35, 1308-1309; Li, A.H.; Dai, L.X.; Hou, X.L.; Chen, M.B. J. Org. Chem., 1996, 61, 3641-4648; Aggarwal, V.K.; Thompsom, A.; Jones, R.V.H.; Standen, M.C.H. J. Org. Chem., 1996, 61, 8368-8369; Hansen, A.; Tagmose, T.M.; Bols, M. Tetrahedron, 1996, 53, 697-706.
15. Bruncko, M.; Khuong, T.A.V.; Sharpless, K.B. Angew. Chem., Int. Ed. Eng., 1996, 35, 454-456; Li, G.C.; Chang, M.T.; Sharpless, K.B. Angew. Chem. Int. Ed. Eng., 1996, 35, 451-454; Reiser, O. Angew. Chem. Int. Ed. Eng., 1996, 35, 1308-1309; Li, A.H.; Dai, L.X.; Hou, X.L.; Chen, M.B. J. Org. Chem., 1996, 61, 3641-4648; Aggarwal, V.K.; Thompsom, A.; Jones, R.V.H.; Standen, M.C.H. J. Org. Chem., 1996, 61, 8368-8369; Hansen, A.; Tagmose, T.M.; Bols, M. Tetrahedron, 1996, 53, 697-706.
16. Bruncko, M.; Khuong, T.A.V.; Sharpless, K.B. Angew. Chem., Int. Ed. Eng., 1996, 35, 454-456; Li, G.C.; Chang, M.T.; Sharpless, K.B. Angew. Chem. Int. Ed. Eng., 1996, 35, 451-454; Reiser, O. Angew. Chem. Int. Ed. Eng., 1996, 35, 1308-1309; Li, A.H.; Dai, L.X.; Hou, X.L.; Chen, M.B. J. Org. Chem., 1996, 61, 3641-4648; Aggarwal, V.K.; Thompsom, A.; Jones, R.V.H.; Standen, M.C.H. J. Org. Chem., 1996, 61, 8368-8369; Hansen, A.; Tagmose, T.M.; Bols, M. Tetrahedron, 1996, 53, 697-706.
17. Bruncko, M.; Khuong, T.A.V.; Sharpless, K.B. Angew. Chem., Int. Ed. Eng., 1996, 35, 454-456; Li, G.C.; Chang, M.T.; Sharpless, K.B. Angew. Chem. Int. Ed. Eng., 1996, 35, 451-454; Reiser, O. Angew. Chem. Int. Ed. Eng., 1996, 35, 1308-1309; Li, A.H.; Dai, L.X.; Hou, X.L.; Chen, M.B. J. Org. Chem., 1996, 61, 3641-4648; Aggarwal, V.K.; Thompsom, A.; Jones, R.V.H.; Standen, M.C.H. J. Org. Chem., 1996, 61, 8368-8369; Hansen, A.; Tagmose, T.M.; Bols, M. Tetrahedron, 1996, 53, 697-706.
18. Bruncko, M.; Khuong, T.A.V.; Sharpless, K.B. Angew. Chem., Int. Ed. Eng., 1996, 35, 454-456; Li, G.C.; Chang, M.T.; Sharpless, K.B. Angew. Chem. Int. Ed. Eng., 1996, 35, 451-454; Reiser, O. Angew. Chem. Int. Ed. Eng., 1996, 35, 1308-1309; Li, A.H.; Dai, L.X.; Hou, X.L.; Chen, M.B. J. Org. Chem., 1996, 61, 3641-4648; Aggarwal, V.K.; Thompsom, A.; Jones, R.V.H.; Standen, M.C.H. J. Org. Chem., 1996, 61, 8368-8369; Hansen, A.; Tagmose, T.M.; Bols, M. Tetrahedron, 1996, 53, 697-706.
19. Bruncko, M.; Khuong, T.A.V.; Sharpless, K.B. Angew. Chem., Int. Ed. Eng., 1996, 35, 454-456; Li, G.C.; Chang, M.T.; Sharpless, K.B. Angew. Chem. Int. Ed. Eng., 1996, 35, 451-454; Reiser, O. Angew. Chem. Int. Ed. Eng., 1996, 35, 1308-1309; Li, A.H.; Dai, L.X.; Hou, X.L.; Chen, M.B. J. Org. Chem., 1996, 61, 3641-4648; Aggarwal, V.K.; Thompsom, A.; Jones, R.V.H.; Standen, M.C.H. J. Org. Chem., 1996, 61, 8368-8369; Hansen, A.; Tagmose, T.M.; Bols, M. Tetrahedron, 1996, 53, 697-706.
20. Vedejs, E.; Lin, S.; Klapars, A.; Wang, J. J. Am. Chem. Soc., 1996, 118, 9796-9797.
21. Hy, A.N.; Cook, P.D. Tetrahedron Lett., 1996, 37, 7233-7236; Ibuka, T. Mimura, N.; Aoyanaa, H.; Akaji, M.; Ohno, H.; Miwa, Y.; Taga, T.; Nakai, T.; Tamamura, H.; Fujii, N.; Yamamoto, Y. J. Org. Chem., 1997, 62, 995-1015; Wipf, P.; Henninger, T.C. J. Org. Chem., 1997, 62, 1586-1587; Miller, S.C.; Scanlan, T.S. J. Am. Chem. Soc., 1997, 119, 2301-2302.
22. Hy, A.N.; Cook, P.D. Tetrahedron Lett., 1996, 37, 7233-7236; Ibuka, T. Mimura, N.; Aoyanaa, H.; Akaji, M.; Ohno, H.; Miwa, Y.; Taga, T.; Nakai, T.; Tamamura, H.; Fujii, N.; Yamamoto, Y. J. Org. Chem., 1997, 62, 995-1015; Wipf, P.; Henninger, T.C. J. Org. Chem., 1997, 62, 1586-1587; Miller, S.C.; Scanlan, T.S. J. Am. Chem. Soc., 1997, 119, 2301-2302.
23. Hy, A.N.; Cook, P.D. Tetrahedron Lett., 1996, 37, 7233-7236; Ibuka, T. Mimura, N.; Aoyanaa, H.; Akaji, M.; Ohno, H.; Miwa, Y.; Taga, T.; Nakai, T.; Tamamura, H.; Fujii, N.; Yamamoto, Y. J. Org. Chem., 1997, 62, 995-1015; Wipf, P.; Henninger, T.C. J. Org. Chem., 1997, 62, 1586-1587; Miller, S.C.; Scanlan, T.S. J. Am. Chem. Soc., 1997, 119, 2301-2302.
24. Hy, A.N.; Cook, P.D. Tetrahedron Lett., 1996, 37, 7233-7236; Ibuka, T. Mimura, N.; Aoyanaa, H.; Akaji, M.; Ohno, H.; Miwa, Y.; Taga, T.; Nakai, T.; Tamamura, H.; Fujii, N.; Yamamoto, Y. J. Org. Chem., 1997, 62, 995-1015; Wipf, P.; Henninger, T.C. J. Org. Chem., 1997, 62, 1586-1587; Miller, S.C.; Scanlan, T.S. J. Am. Chem. Soc., 1997, 119, 2301-2302.
25. Jenny, E.F.; Druey, J. Angew. Chem., Int. Ed. Eng., 1962, 1, 155-156.
26. Pine, S.H. Org. React., 1970, 18, 403-464.