The Asymmetric Horner-Wadsworth-Emmons Reaction Mediated by an External Chiral Ligand

Angewandte Chemie - International Edition

Volumn 37, Issue 4, 1998, Pages 515-517

  Mizuno, Masashi ^a   Fujii, Kunihiko ^a   Tomioka, Kiyoshi ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

Asymmetric synthesis; Carbanions; Lithium; Olefinations

Indexed keywords

EID: 0032473521     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(sici)1521-3773(19980302)37:4<515::aid-anie515>3.3.co;2-h     Document Type: Article

References (33)

1. a) L. Horner, Pure Appl. Chem. 1964, 9, 225-244;
2. b) W. S. Wadsworth, Jr., W. D. Emmons, J. Am. Chem. Soc. 1961, 83, 1733-1738;
3. c) W. S. Wadsworth, Jr., Organic Reactions, Vol. 25, Wiley, New York, 1977, pp. 73-253;
4. d) K. C. Nicolaou, M. W. Härter, J. L. Cunzner, A. Nadin, Liebigs Ann. 1997, 1283-1301;
5. e) E. L. Eliel, S. H. Wilen, Stereochemistry of Organic Compounds, Wiley, New York, 1994, chap. 14.
6. a) H. J. Bestmann, J. Lienert, Angew. Chem. 1969, 81, 751-752; Angew. Chem. Int. Ed. Engl. 1969, 8, 763-764;
7. a) H. J. Bestmann, J. Lienert, Angew. Chem. 1969, 81, 751-752; Angew. Chem. Int. Ed. Engl. 1969, 8, 763-764;
8. b) B. M. Trost, D. P. Curran, J. Am. Chem. Soc. 1980, 102, 5699-5700.
9. N. J. S. Harmat, S. Warren, Tetrahedron Lett. 1990, 31, 2743-2746.
10. S. Hanessian, S. Beaudoin, Tetrahedron Lett. 1992, 33, 7655-7658.
11. S. E. Denmark, C.-T. Chen, J. Am. Chem. Soc. 1992, 114, 10674-10676.
12. a) T. Takahashi, M. Matsui, N. Maeno, T. Koizumi, Heterocycles, 1990, 30, 353-357;
13. b) K. Narasaka, E. Hidai, Y. Hayashi, J.-L. Gras, J. Chem. Soc. Chem. Commun. 1993, 102-104;
14. c) K. Tanaka, Y. Ohta, K. Fuji, T. Taga, Tetrahedron Lett. 1993, 34, 4071-4074.
15. a) I. Tömösközi, G. Janzso, Chem. Ind. (London) 1962, 2085-2086;
16. b) H.-J. Gais, G. Schmiedl, W. A. Ball, J. Bund, G. Hellmann, I. Erdelmeier. Tetrahedron Lett. 1988, 29, 1773-1774;
17. c) H. Rehwinkel, J. Skupsch, H. Vorbrüggen, ibid. 1988, 29, 1775-1776;
18. d) N. Kann, T. Rein, J. Org. Chem. 1993, 58, 3802-3804;
19. e) T. Furuta, M. Iwamura, J. Chem. Soc. Chem. Commun 1994, 2167-2168;
20. f) T. Mandai, Y. Kaihara, J. Tsuji, J Org. Chem. 1994, 59, 5847-5849.
21. A. Abiko, S. Masamune, Tetrahedron Lett. 1996, 37, 1077-1080.
22. F. Toda, H. Akai, J. Org. Chem. 1990, 55, 3446-3447.
23. T. Kumamoto, K. Koga, Chem. Pharm. Bull. 1997, 45, 753-755.
24. K. Tomioka, Synthesis 1990, 541-549.
25. H. Fujieda, M. Kanai, T. Kambara, A. Iida, K. Tomioka, J. Am. Chem. Soc. 1997, 119, 2060-2061.
26. Phosphonates used in this work were prepared by the Arbuzov reaction.
27. There are many examples for the equatorial attack of phosphonate anions.[4,5] The signals for benzylmethyl protons in 6 and 7 appeared at δ = 3.09 and 3.50, consistent with literature values; see also J. E. Anderson, J. Chem. Soc. Perkin 2 1974, 10-13.
28. All new compounds were fully characterized.
29. [5a] led to recovery of the starting alcohol, not to 8.
30. A. Pfaltz, Acc. Chem. Res. 1993, 26, 339-345.
31. P. Beak, A. Basu, D. J. Gallagher, Y. S. Park, S. Thayumanavan, Acc. Chem. Res. 1996, 29, 552-560.
32. Repeated experiments without warming to O C also led to slightly decreased ee values.
33. M. Duraisamy, H. M. Walborsky, J. Am. Chem. Soc. 1983, 105, 3252-3264.