Nonenzymatic kinetic resolution of 1,2-diols catalyzed by an organotin compound

Organic Letters

Volumn 1, Issue 7, 1999, Pages 969-972

  Iwasaki, Fumiaki ^a   Maki, Toshihide ^b   Nakashima, Waka ^b   Onomura, Osamu ^b   Matsumura, Yoshihiro ^c  

^a TOKUYAMA CORPORATION   (Japan)

^b NAGASAKI UNIVERSITY   (Japan)

^c KYUSHU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0011249788     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol9908373     Document Type: Article

References (31)

1. (a) Vedejs, E.; Daugulis, O.; Diver, S. T. J. Org. Chem. 1996, 61, 430.
2. (b) Ruble, J. C.; Fu, G. C. J. Org. Chem. 1996, 61, 7230.
3. (c) Oriyama, T.; Hori, Y.; Imai, K.; Sasaki, R. Tetrahedron Lett. 1996, 37, 8543.
4. (d) Ruble, J. C.; Latham, H. A.; Fu, G. C. J. Am. Chem. Soc. 1997, 119, 1492.
5. (e) Kawabata, T.; Nagao, M.; Takasu, K.; Fuji, K. J. Am. Chem. Soc. 1997, 119, 3169.
6. (f) Copeland, G. T.; Jarvo, E. R.; Miller, S. J. J. Org. Chem. 1998, 63, 6784.
7. (a) Oriyama, T.; Imnai, K.; Hosoya, T.; Sano, T. Tetrahedron Lett. 1998, 39, 397.
8. (b) Oriyama, T.; Imai, K.; Sano, T.; Hosoya, T. Tetrahedron Lett. 1998, 39, 3529.
9. (c) Otera, J.; Sakamoto, K.; Tsukamoto, T.; Orita, A. Tetrahedron Lett. 1998, 39, 3201.
10. (a) Chenault, H. K.; Chafin, L. F.; Liehr, S. J. Org. Chem. 1998, 63, 4039.
11. (b) Egri, G.; Baitzz-Gács, E.; Poppe, L. Tetrahedron: Asymmetry 1996, 7, 1437.
12. (c) Theil, F.; Weidner, J.; Ballschuh, S.; Kunath, A.; Schick, H. J. Org. Chem. 1994, 59, 388.
13. (d) Weidner, J.; Theil, F.; Schick, H. Tetrahedron: Asymmetry 1994, 5, 751.
14. (e) Theil, F.; Weidner, J.; Ballschuh, S.; Kunath, A.; Schick, H. Tetrahedron Lett. 1993, 34, 305.
15. (f) Theil, F.; Ballschuh, S.; Kunath, A.; Schick H. Tetrahedron: Asymmetry 1991, 2, 1031.
16. Maki, T.; Iwasaki, F.; Matsumura, Y. Tetrahedron Lett. 1998, 39, 5601.
17. Noyori, R.; Kitamura, M.; Takemoto, K. Japan Kokai Tokkyo Koho JP 04-91093, 1992; Chem. Abstr. 1992, 117, 171695u.
18. Noyori, R.; Kitamura, M.; Takemoto, K. Japan Kokai Tokkyo Koho JP 04-91093, 1992; Chem. Abstr. 1992, 117, 171695u.
19. (a) Nanni, D.; Curran, D. P. Tetrahedron: Asymmetry 1996, 7, 2417.
20. (b) Maigrot, N.; Mazaleyrat, J.-P. Synthesis 1985, 317.
21. Brown, J. M.; Murrer, B. A. J. Chem. Soc., Perkin Trans. 2 1982, 489.
22. (R)-Enantiomer-enriched 3a with 0-59% ee was generated.
23. Potassium carbonate was usable. Satisfactory results were obtained by using solid bases pulverized as small as possible.
24. Kagan, H. B.; Fiaud, J. C. Top. Stereochem. 1988, 18, 249.
25. There has recently appeared an interesting temperature-dependent switching of enantioselectivity (<42.3% ee) in a desymmetric carbamoylation of 2-substituted 1,3-propanediol using catalyst A; see ref 2c. However, the enantioselectivity in A-catalyzed benzoylation of the 1,3-diol was 0% in our hand.
26. Acylation of dibutylstannylene acetals was well documented, for example: (a) Hanessian, S.; David, S. Tetrahedron 1985, 41, 643 and references therein.
27. (b) Ricci, A.; Roelens, S.; Vannucchi, A. J. Chem. Soc., Chem. Commun. 1985, 1457.
28. (c) Roelens, S. J. Chem. Soc., Perkin Trans 2 1988, 1617.
29. (d) Reginato, G.; Ricci, A.; Roelens, S.; Scapecchi, S. J. Org. Chem. 1990, 55, 5132.
30. (e) Roelens, S. J. Org. Chem. 1996, 61, 5257.
31. (f) Hanessian, S.; Reinhold, U.; Gentile, G. Angew. Chem., Int. Ed. Engl. 1997, 36, 1881.