Synthesis of optically active allenes using tandem enzyme and palladium-catalysed reactions

Chemical Communications

Volumn , Issue 21, 1997, Pages 2083-2084

  Dixneuf, Pierre H ^a   Guyot, Thierry ^b   Ness, Mark D ^b   Roberts, Stanley M ^b  

^a UNIVERSITÉ DE RENNES 1   (France)

^b UNIVERSITY OF LIVERPOOL   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002500927     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/a704374k     Document Type: Article

References (25)

1. Chemistry of the Allenes, vol. 1-3, ed. S. R. Landor, Academic Press, New York, 1982;
2. H. F. Schuster and G. M. Coppola, Allenes in Organic Synthesis, Wiley-Interscience, New York, 1984;
3. C. Bruneau and P. H. Dixneuf, Allenes and Cumulenes, in Comprehensive Organic Functional Group Transformations, ed. A. R. Katritzky, O. Meth-Cohn and C. W. Rees, Pergamon, Oxford, 1995, vol. l, ch. 20.
4. A. G. Myers and B. Zheng, Tetrahedron Lett., 1996, 37, 4841;
5. J. Am. Chem. Soc., 1996, 118, 4492;
6. J. Tsuji and T. Mandai, Synthesis, 1996, 1;
7. see also J. Tsuji, Palladium Reagents and Catalysts: Innovation in Chemical Synthesis, Wiley, New York, 1995.
8. For earlier papers detailing resolutions of secondary propargyl alcohols-acetates, see C. Chan, P. B. Cox and S. M. Roberts, J. Chem. Soc., Chem. Commun., 1988, 971;
9. M. Shimizu, H. Kawanami and T. Fujisawa, Chem. Lett., 1992, 107;
10. K. Burgess and L. D. Jennings, J. Am. Chem. Soc., 1991, 113, 6129.
11. T. Mandai, T. Matsumoto, R. Kawada and J. Tsuji, Tetrahedron Lett., 1993, 34, 2161;
12. T. Mandai, T. Nakata, H. Murayama, H. Yamaoki, M. Ogawa, M. Kawada and J. Tsuji, Tetrahedron Lett., 1990, 31, 7179.
13. C. Darcel, S. Bartsch, C. Bruneau and P. H. Dixneuf, Synlett, 1994, 457;
14. cf. J. A. Marshall and M. A. Wolf, J. Org. Chem., 1996, 61, 3238.
15. C. J. Elsevier, P. M. Stehouwer, H. Westmijze and P. Vermeer, J. Org. Chem., 1983, 48, 1103.
16. F. Toda, K. Tanaka, H. Ueda and T. Oshima, Isr. J. Chem., 1985, 25, 338;
17. Tetrahedron Lett., 1981, 22, 4664;
18. tertiary propargyl alcohols are not readily resolved in high ee using enzyme-catalysed acylation procedures; see I. Brackenridge, R. McCague, S. M. Roberts and N. J. Turner, J. Chem. Soc., Perkin Trans. 1, 1993, 1093;
19. D. O'Hagan and N. A. Zaidi, Tetrahedron: Asymmetry, 1994, 5, 111.
20. M. Alami, F. Ferri and G. Linstrumelle, Tetrahedron Lett., 1993, 34, 6403.
21. Cf. B. I. Glanzer, K. Faber and H. Griengl, Tetrahedron, 1987, 43, 5791.
22. H. C. Brown and G. G. Pai, J. Org. Chem., 1982, 47, 1606;
23. P. Bartmettler and H. J. Hansen, Helv. Chim. Acta., 1990, 73, 1515.
24. A. Mannscheck, W. Munninger, T. Burgemeister, J. Gore and B. Cazes, Tetrahedron, 1986, 42, 399.
25. R. Rossi and P. Diversi, Synthesis, 1973, 25.