Enantioselective synthesis of bis-α-amino acid esters via asymmetric phase-transfer catalysis

Tetrahedron Letters

Volumn 40, Issue 7, 1999, Pages 1385-1388

  Lygo, B ^a   Crosby, J ^a   Peterson, J A ^a  

^a UNIVERSITY OF SALFORD   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ALPHA AMINO ACID; AMINO ACID DERIVATIVE; ANTINEOPLASTIC ANTIBIOTIC; DIPEPTIDYL CARBOXYPEPTIDASE INHIBITOR;

ARTICLE; CATALYSIS; DRUG STRUCTURE; DRUG SYNTHESIS; STEREOCHEMISTRY;

EID: 0033547930     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)02615-X     Document Type: Article

References (40)

1. S.O Andersen Biochim. Biophys. Acta 93 1964 213
2. S.C Fry Biochem. J. 204 1982 449
3. R Cox J. Nat. Prod. Rep. 13 1996 29
4. G.S Scapin J.S Blanchard Adv. Enzymol. 72 1997 279
5. H Kase M Kaneko K Yamada J. Antibiot. 40 1987 450
6. T Yasuzawa K Shirahata H Sano J. Antibiot. 40 1987 455
7. S.D Jolad J.J Hoffmann S.J Torrance R.M Wiedhopf J.R Cole S.K Arora R.B Bates R.L Gargiulo G.R Kriek J. Am. Chem. Soc. 99 1977 8040
8. A Ritzén T Frejd J. Chem. Soc., Perkin Trans. I 1998 3419
9. R.F Nutt D.F Veber R Saperstein J. Am. Chem. Soc. 102 1980 6539
10. See: P.L DeMarsh G.I Wells T.F Lewandowski C.L Frey P.K Bhatnagar E.J.R Ostovic J. Infect. Dis. 173 1996 203 and references therein
11. W.R Paukovits O.D Laerum Hoppe-Seyler's Z. Physiol. Chem. 365 1984 303
12. B Lygo J Crosby T.R Lowdon P.G Wainwright Tetrahedron Lett. 38 1997 2343
13. B Lygo P.G Wainwright Tetrahedron Lett. 38 1997 8595
14. B Lygo P.G Wainwright Tetrahedron Lett. 39 1998 1599
15. For the use of closely related catalysts in the enantioselective alkylation of glycine imines under solid-liquid phase-transfer conditions see: E.J Corey F Xu M.C Noe J. Am. Chem. Soc. 119 1997 12414
16. E.J Corey M.C Noe F Xu Tetrahedron Lett. 39 1998 5347
17. For previous work on the enantioselective alkylation of glycine imines under liquid-liquid phase-transfer conditions see: I.A Esikova T.S Nahreini M.J O'Donnell M.E. Halpern ACS Symposium Series 659: Phase-Transfer Catalysis - Mechanisms and Syntheses 1997 ACS Washington D.C 89
18. M.J O'Donnell I.A Esikova A Mi D.F Shullenberger S Wu M.E. Halpern ACS Symposium Series 659: Phase-Transfer Catalysis - Mechanisms and Syntheses 1997 ACS Washington D.C 124
19. O'Donnell, M.J; Wu, S; Esikova, I; Mi, A. U.S. Patent 5,554,753 , September 10, 1996
20. M.J O'Donnell S Wu J.C Huffman Tetrahedron 50 1994 4507
21. K Tohdo Y Hamada T Shioiri Synlett 1994 247
22. B Imperiali S.L Fisher J. Org. Chem. 57 1992 757
23. K Tohdo Y Hamada T Shioiri Pept. Chem. 1991 7
24. M.J O'Donnell W.D Bennett S Wu J. Am. Chem. Soc. 111 1989 2353
25. M.J O'Donnel F Delgado C Hostettler R Schwesinger For a recent report on the use of catalysts of this type in the homogeneous enantioselective alkylation of glycine inmines see: Tetrahedron Lett. 39 1998 8775
26. For leading references on previous synthetic approaches to simple bis-α-amino acids of type ( 8 ) see: Y Gao P Lane-Bell J.C Vederas J. Org. Chem. 63 1998 2133
27. R.M Williams J Liu J. Org. Chem. 63 1998 2130
28. J Hiebl M Blanka A Guttman H Kollmann K Leitner G Mayrhofer F Rovenszky K Winkler Tetrahedron 54 1998 2059
29. P Kremminger K Undheim Tetrahedron 53 1997 6925
30. K Hammer T Benneche H Hope K Undheim Acta. Chem. Scand. 51 1997 392
31. A Mazón C Nájera J Ezquerra C Pedregal Tetrahedron Lett. 36 1995 7697
32. J.E Baldwin V Lee C.J Schofield Synlett 1992 249
33. R.M Williams M-N Im J Cao J. Am. Chem. Soc. 113 1991 6976
34. A-S Carlström T Frejd J. Org. Chem. 56 1991 1289
35. G Bold R.O Duthaler M Riediker Angew. Chem. Int. Ed. 28 1989 497
36. R Fitzi D Seebach Tetrahedron 44 1988 5277
37. W Ried B Schleimer Ann. Chem. 639 1961 68
38. A.W Burgstahler C.E Aiman J. Org. Chem. 25 1960 489
39. K Schlögl Monatsh. Chem. 89 1958 377
40. J.H Burckhalter V.C Stephens J. Am. Chem. Soc. 73 1951 56