Rational design of chiral catalysis for the enantioselective addition reaction of dialkylzincs

Enantiomer

Volumn 4, Issue 6, 1999, Pages 591-598

  Soai, Kenso ^a  

^a TOKYO UNIVERSITY OF SCIENCE   (Japan)

Author keywords

Alkylation; Asymmetric autocatalysis; Conjugate addition; Dialkylzincs; Enantioselective catalysis

Indexed keywords

ACETONITRILE; ALCOHOL; ALDEHYDE; ALKANOL; ALKYL GROUP; METHANOL DERIVATIVE; NOREPHEDRINE; PYRIDINE DERIVATIVE; PYRIMIDINE DERIVATIVE; QUINOLINE DERIVATIVE; SOLVENT; ZINC DERIVATIVE;

CATALYSIS; CATALYST; CHEMICAL REACTION; CHIRALITY; ENANTIOMER; PRIORITY JOURNAL; REVIEW; STEREOCHEMISTRY;

EID: 0033375376     PISSN: 10242430     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Review

References (44)

1. Reviews: (a) K. Soai and S. Niwa. Chem. Rev., 1992, 92, 833;
2. (b) K. Soai and T. Hayase. Yuki Gosei Kagaku Kyokaishi (J. Synth. Org. Chem., Jpn.), 1995, 53, 138;
3. (c) R. Noyori and M. Kitamura. Angew. Chem. Int. Ed. Engl., 1991, 30, 49;
4. (d) K. Soai and T. Shibata. Yuki Gosei Kagaku Kyokaishi (J. Synth. Org. Chem., Jpn.), 1997, 55, 994;
5. (e) K. Soai and T. Shibata in Organozinc Reagents, Eds. Knochel, P. and Jones, P. Chap. 12, Oxford University Press, New York, 1999, pp. 245-261.
6. T. Mukaiyama, K. Soai, T. Sato, H. Shimizu and K. Suzuki. J. Am. Chem. Soc., 1979, 101, 1455.
7. (a) K. Soai, S. Yokoyama, K. Ebihara and T. Hayasaka. J. Chem. Soc., Chem. Commun., 1987, 1690;
8. (b) K. Soai, S. Yokoyama and T. Hayasaka. J. Org. Chem., 1991, 56, 4264;
9. (c) K. Soai, T. Hayase, K. Takai and T. Sugiyama. J. Org. Chem., 1994, 59, 7903;
10. (d) K. Soai, T. Konishi and T. Shibata. Heterocycles, 1999, 51, 1421.
11. (a) A.S. Thompson, E.G. Corley, M.F. Huntington and E.J.J. Grabowski. Tetrahedron Lett., 1995, 36, 8937;
12. (b) A.S. Thompson, E.G. Corley, M.F. Huntington, E.J.J. Grabowski, J.F. Remenar and D.B. Collum. J. Am. Chem. Soc., 1998, 120, 2028;
13. (c) M.E. Pierce, R.L. Parsons Jr., L.A. Radesca, Y.S. Lo, S. Silverman, J.R. Moore, Q. Islam, A. Choudhury, J.M.D. Fortunak, D. Nguyen, C. Luo, S.J. Morgan, W.P. Davis, P.N. Confalone, C. Chen, R.D. Tillyer, L. Frey, L. Tan, F. Xu and D. Zhao. J. Org. Chem., 1998, 63, 8536;
14. (d) L. Tan, C. Chen, R.D. Tillyer, E.J.J. Grabowski and P.J. Reider. Angew. Chem. Int. Ed., 1999, 38, 711.
15. (a) K. Soai and A. Ookawa. J. Chem. Soc., Chem. Commun., 1986, 412;
16. (b) A. Ookawa and K. Soai. J. Chem. Soc., Perkin Trans. 1, 1987, 1465.
17. (a) K. Soai, A. Ookawa, K. Ogawa and T. Kaba. J. Chem. Soc., Chem. Commun., 1987, 467;
18. (b) K. Soai, A. Ookawa, T. Kaba and K. Ogawa. J. Am. Chem. Soc., 1987, 109, 7111.
19. (a) For the implications: H. Wynberg. J. Macromol. Soc. Chem., Sect. A, 1989, 26, 1033;
20. (b) Short review: C. Bolm, F. Bienewald and A. Seger. Angew. Chem. Int. Ed. Engl., 1996, 35, 1657.
21. K. Soai, S. Niwa and T. Kobayashi. J. Chem. Soc., Chem. Commun., 1987, 801.
22. K. Soai, S. Hori and S. Niwa. Heterocycles, 1989, 29, 2965.
23. K. Soai, S. Niwa and H. Hori. J. Chem. Soc., Chem. Commun., 1990, 982.
24. T. Shibata, H. Morioka, S. Tanji, T. Hayase, Y. Kodaka and K. Soai. Tetrahedron Lett., 1996, 37, 8783.
25. (a) T. Shibata, K. Choji, H. Morioka, T. Hayase and K. Soai. Chem. Commun., 1996, 751;
26. (b) T. Shibata, K. Choji, T. Hayase, Y. Aizu and K. Soai. Chem. Commun., 1996, 1235.
27. (a) K. Soai, T. Hayase, C. Shimada and K. Isobe. Tetrahedron: Asymmetry, 1994, 5, 789;
28. (b) K. Soai, T. Hayase and K. Takai. Tetrahedron: Asymmetry, 1995, 6, 637.
29. T. Shibata, H. Morioka, T. Hayase, K. Choji and K. Soai. J. Am. Chem. Soc., 1996, 118, 471.
30. T. Shibata, S. Yonekubo and K. Soai. Angew. Chem. Int. Ed., 1999, 38, 659.
31. (a) C. Puchot, O. Samuel, E. Dunach, S. Zhao, C. Agami and H.B. Kagan. J. Am. Chem. Soc., 1986, 108, 2353;
32. (b) N. Oguni, Y. Matsuda and T. Kaneko. J. Am. Chem. Soc., 1988, 110, 7877;
33. c) M. Kitamura, S. Okada and R. Noyori. J. Am. Chem. Soc., 1989, 111, 4028;
34. (d) For a recent review, C. Girard and H.B. Kagan. Angew. Chem. Int. Ed., 1998, 37, 2922.
35. (a) K. Soai, T. Shibata, H. Morioka and K. Choji. Nature (London), 1995, 378, 767;
36. (b) T. Shibata, T. Hayase, J. Yamamoto and K. Soai. Tetrahedron: Asymmetry, 1997, 8, 1717.
37. Review: B.E. Rossiter and N.M. Swingle. Chem. Rev., 1992, 92, 771.
38. (a) K. Soai, S. Yokoyama, T. Hayasaka and K. Ebihara. J. Org. Chem., 1988, 53, 4148;
39. (b) K. Soai, T. Hayasaka, S. Ugajin and S. Yokoyama. Chem. Lett., 1988, 1571;
40. (c) K. Soai, T. Hayasaka and S. Ugajin. J. Chem. Soc., Chem. Commun., 1989, 516;
41. (d) K. Soai, M. Okudo and M. Okamoto. Tetrahedron Lett., 1991, 32, 95.
42. (a) C. Bolm, M. Ewald and M. Felder. Chem. Ber., 1992, 125, 1205;
43. (b) A.H.M. deVries, J.F.G.A. Jansen and B.L. Feringa. Tetrahedron, 1994, 50, 4479.
44. T. Shibata, J. Yamamoto, N. Matsumoto, S. Yonekubo, S. Osanai and K. Soai. J. Am. Chem. Soc., 1998, 120, 12157.