Regioselective nucleophilic ring opening reactions of 2,2-disubstituted aziridines - The asymmetric synthesis of α,α-disubstituted amino acids

Tetrahedron

Volumn 52, Issue 40, 1996, Pages 13035-13050

  Burgaud, Beatrice G M ^a   Horwell, David C ^a   Padova, Allessandro ^a   Pritchard, Martyn C ^a  

^a UNIVERSITY OF CAMBRIDGE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID DERIVATIVE;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; PRIORITY JOURNAL; REACTION ANALYSIS; TECHNIQUE;

EID: 0030607173     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(96)00784-3     Document Type: Article

References (21)

1. 1. See Burgaud, B. G. M.; Horwell, D. C.; Pritchard, M. C.; Bernad, N.; Martinez, J. Tetrahedron : Asymmetry 1995, 6, 1081 and references cited therein.
2. 2. Horwell, D. C.; Pritchard, M. C.; Raphy, J.; Ratcliffe, G. Immunopharmacology 1996, 33, 68.
3. 3. Horwell, D. C.; Hughes, J.; Hunter, J. C.; Pritchard, M. C.; Richardson, R. S.; Roberts, E.; Woodruff, G. N. J. Med. Chem. 1991, 34, 404.
4. 4. Boden, P.; Eden, J. M.; Hodgson, J.; Horwell, D. C.; Pritchard, M. C.; Raphy, J.; Suman-Chauhan, N. Bioorg. Med. Chem. Lett. 1995, 5, 1773.
5. 5. Horwell, D. C.; Ratcliffe, G. S.; Roberts, E. Bioorg. Med. Chem. Lett. 1991, 1, 169.
6. 6. Higginbottom, M.; Kneen, C.; Ratcliffe, G. S. J. Med. Chem. 1992, 35, 1572.
7. 7. For an overview see Williams, R. M. Synthesis of Optically Active Amino Acids; Pergamon Press: Oxford. 1989; Vol. 7 and Heimgartner, H. Angew Chem. Int. Ed. Engl. 1991, 30, 238.
8. 7. For an overview see Williams, R. M. Synthesis of Optically Active Amino Acids; Pergamon Press: Oxford. 1989; Vol. 7 and Heimgartner, H. Angew Chem. Int. Ed. Engl. 1991, 30, 238.
9. 8. For a recent review see Tanner, D. Angew. Chem. Int. Ed. Engl. 1994, 33, 599.
10. 9. Wipf, P.; Venkatraman, S.; Miller, C. P. Tetrahedron Lett. 1995, 36, 3639.
11. 10. Shao, H.; Zhu, Q.; Goodman, M. J. Org. Chem. 1995, 60, 790.
12. 11. Solomon, M. E.; Lynch, C. L.; Rich, D. H. Tetrahedron Lett. 1995, 36, 4955.
13. 12. Stamm, H.; Assithianakis, P.; Buchholz, B.; Weiβ, R. Tetrahedron Lett. 1982, 23, 5021.
14. 13. Baldwin, J. E.; Spivey, A. C.; Schofield, C. J.; Sweeney, J. B. Tetrahedron 1993, 49, 6309;
15. a) Baldwin, J. E.; Farthing, C. N.; Russell, A. T.; Schofield, C. J.; Spivey, A. C. Tetrahedron Lett. 1996, 37, 3761.
16. 14. Stewart, J. J. P. J. Computer-Aided Mol. Des 1990, 4, 1.
17. 15. Lin, F-Y.; Bellos, K.; Stamm, H.; Onistschenko, A Tetrahedron 1992, 48, 2359.
18. 16. Church, N. J.; Young, D. W. Tetrahedron Lett. 1995, 36, 151.
19. 17. a) Legters, J.; Thijs, L.; Zwanenburg, B. Recl. Trav. Chim. Pays-Bas 1992, 111, 1;
20. b) Dauban, P.; Dubois, L.; Tran Huu Dau, M. E.; Dodd, R. H. J. Org. Chem. 1995, 60, 2035.
21. 18. Yoshihiko, I.; Sawamura, M.; Shirakawa, E.; Hayashizaki, K.; Hayashi, T. Tetrahedron, 1988, 44(17), 5253.