Lipase-catalyzed enantioselective acylation of prochiral 2-(ω)-phosphono)alkyl-1,3-propanediols: Application to the enantioselective synthesis of ω-phosphono-α-amino acids

Tetrahedron Asymmetry

Volumn 7, Issue 9, 1996, Pages 2743-2754

  Yokomatsu, Tsutomu ^a   Sato, Mutsumi ^a   Shibuya, Shiroshi ^a  

^a TOKYO UNIVERSITY OF PHARMACY AND LIFE SCIENCES   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID DERIVATIVE; PROPANEDIOL DERIVATIVE; TRIACYLGLYCEROL LIPASE;

ACETYLATION; ARTICLE; CATALYSIS; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030249820     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/0957-4166(96)00354-0     Document Type: Article

References (22)

1. 1. a) Engel, R. Chem. Rev. 1977, 77, 349.
2. b) Engel, R. The Role of Phosphonates in Living Systems, Hinderbrand, R. L., Ed., CRC Press, Boca Raton, FL 1983, pp 93-138.
3. 2. Schoepp, D. D.; Johnson, B. G. J. Neurochem. 1989, 53, 273;
4. 3. a) Smith, E. C.; McQuaid, L. A. J. Org. Chem. 1990, 55, 4472;
5. b) Minowa, N.; Hirayama, M.; Fukatsu, S. Tetrahedron Lett. 1984, 25, 1147;
6. c) Koerner, J. R; Cotman, C. W. Brain Research 1981, 216, 192;
7. d) Kukhar', V. P.; Soloshonok, V. A.; Solodenko, V. A. Phosphorus, Sulfur, and Silicon 1994, 92, 239 and references cited therein.
8. 4. a) Berkowitz, D. B.; Shen, Q.; Maeng, J.-H. Tetrahedron Lett. 1994, 35, 6445.
9. b) Otaka, A.; Miyoshi, K.; Burke, T. R., Jr.; Roller, P. P.; Kubota, H.; Tamamura, H.; Fujii, N. Tetrahedron Lett. 1995, 36, 927.
10. 5. For reviews on lipase-catalyzed enantioselective acylations and related reactions: Xie, Z.-F. Tetrahedron: Asymmetry 1991, 2, 733. Faber, K.; Riva, S. Synthesis 1992, 895. Theil, F. Chem. Rev. 1995, 95, 2203. Schoffers, E.; Golebiowski, A.; Johnson, C. R. Tetrahedron 1996, 52, 3769.
11. 5. For reviews on lipase-catalyzed enantioselective acylations and related reactions: Xie, Z.-F. Tetrahedron: Asymmetry 1991, 2, 733. Faber, K.; Riva, S. Synthesis 1992, 895. Theil, F. Chem. Rev. 1995, 95, 2203. Schoffers, E.; Golebiowski, A.; Johnson, C. R. Tetrahedron 1996, 52, 3769.
12. 5. For reviews on lipase-catalyzed enantioselective acylations and related reactions: Xie, Z.-F. Tetrahedron: Asymmetry 1991, 2, 733. Faber, K.; Riva, S. Synthesis 1992, 895. Theil, F. Chem. Rev. 1995, 95, 2203. Schoffers, E.; Golebiowski, A.; Johnson, C. R. Tetrahedron 1996, 52, 3769.
13. 5. For reviews on lipase-catalyzed enantioselective acylations and related reactions: Xie, Z.-F. Tetrahedron: Asymmetry 1991, 2, 733. Faber, K.; Riva, S. Synthesis 1992, 895. Theil, F. Chem. Rev. 1995, 95, 2203. Schoffers, E.; Golebiowski, A.; Johnson, C. R. Tetrahedron 1996, 52, 3769.
14. 6. Dubois, J.; Fourès, C; Bory, S.; Falcou, S.; Gaudry, M.; Marquet, A. Tetrahedron 1991, 47, 1001.
15. 7. a) Berkowitz, D. B.; Eggen, M.; Shen, Q.; Sloss, D. G. J. Org. Chem. 1993, 58, 6174.
16. b) Shen, Q.; Sloss, D. G.; Berkowitz, D. B. Synth. Commun. 1994, 24, 1519.
17. 8. Lipase A and lipase AY (Candida cylindracea) were totally ineffective on the transesterification reaction.
18. 9. Carlsen, P. H.; Katsuki, T.; Martin, V. S. Sharpless, K. B. J. Org. Chem. 1981, 46, 3936. Partial racemization was observed when the oxidation was carried out with Jones reagent. The Ru-catalyzed oxidation minimized the partial racemization.
19. 10. Ninomiya, K.; Shioiri, T.; Yamada, S. Tetrahedron 1974, 30, 2151.
20. 11. Yield is not optimized.
21. 12. Weissfloch, A. N. E.; Kazlauskas, R. J. J. Org. Chem. 1995, 60, 6959.
22. 13. Soborovskii, L. Z.; Baina, N. F, J. Gen. Chem. U.S.S.R. (Engl. Transl.) 1959, 29, 1115.