Generation of oxiranyllithiums and oxiranyl Grignard reagents having a carbanion-destabilizing group from sulfinyloxiranes: Their property and an application to asymmetric synthesis of epoxides and alcohols

Tetrahedron

Volumn 55, Issue 9, 1999, Pages 2515-2528

  Satoh, Tsuyoshi ^a   Kobayashi, Shigeko ^a   Nakanishi, Shino ^a   Horiguchi, Kyoko ^a   Irisa, Shiro ^a  

^a TOKYO UNIVERSITY OF SCIENCE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CARBANION; LITHIUM DERIVATIVE; SULFOXIDE; UNCLASSIFIED DRUG;

ARTICLE; BINDING KINETICS; ISOMERISM; LIGAND BINDING; ORGANIC CHEMISTRY; PRIORITY JOURNAL; REACTION ANALYSIS; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0033605190     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(99)00038-1     Document Type: Article

References (40)

1. Rao, A. S.; Paknikar, S. K.; Kirtane, J. G. Tetrahedron 1983, 39, 2323. Gorzynski-Smith, J.Synthesis 1984, 629. Lewars, E. G. In "Comprehensive Heterocyclic Chemistry" Katritzky, A. R.; Rees, C. W. Eds; Pergamon Press: Oxford, 1984; Vol. 7, p 95. Wong, H. N. C.; Fork, C. C. M.; Wong, T. Heterocycles 1987, 26, 1345.
2. Rao, A. S.; Paknikar, S. K.; Kirtane, J. G. Tetrahedron 1983, 39, 2323. Gorzynski-Smith, J. Synthesis 1984, 629. Lewars, E. G. In "Comprehensive Heterocyclic Chemistry" Katritzky, A. R.; Rees, C. W. Eds; Pergamon Press: Oxford, 1984; Vol. 7, p 95. Wong, H. N. C.; Fork, C. C. M.; Wong, T. Heterocycles 1987, 26, 1345.
3. Rao, A. S.; Paknikar, S. K.; Kirtane, J. G. Tetrahedron 1983, 39, 2323. Gorzynski-Smith, J.Synthesis 1984, 629. Lewars, E. G. In "Comprehensive Heterocyclic Chemistry" Katritzky, A. R.; Rees, C. W. Eds; Pergamon Press: Oxford, 1984; Vol. 7, p 95. Wong, H. N. C.; Fork, C. C. M.; Wong, T. Heterocycles 1987, 26, 1345.
4. Rao, A. S.; Paknikar, S. K.; Kirtane, J. G. Tetrahedron 1983, 39, 2323. Gorzynski-Smith, J.Synthesis 1984, 629. Lewars, E. G. In "Comprehensive Heterocyclic Chemistry" Katritzky, A. R.; Rees, C. W. Eds; Pergamon Press: Oxford, 1984; Vol. 7, p 95. Wong, H. N. C.; Fork, C. C. M.; Wong, T. Heterocycles 1987, 26, 1345.
5. Crandall, J. K.; Apparu, M. Org. React. 1983, 29, 354.
6. Satoh, T. Chem. Rev. 1996, 96, 3303.
7. Eisch, J. J.; Galle, J. E. J. Am. Chem. Soc. 1976, 95, 4646. Eisch, J. J.; Galle, J. E. J. Organomet. Chem. 1976, 121, c-10,
8. Eisch, J. J.; Galle, J. E. J. Am. Chem. Soc. 1976, 95, 4646. Eisch, J. J.; Galle, J. E. J. Organomet. Chem. 1976, 121, c-10,
9. Burford, C.; Cooke, F.; Roy, G.; Magnus, P. Tetrahedron 1983, 39, 867. Molander, G. A.; Mautner, K. J. Org. Chem. 1989, 54, 4042. Molander, G. A.; Mautner, K. Pure Appl. Chem. 1990, 62, 707. Murthi, K. K.; Salomon, R. G. Tetrahedron Lett. 1994, 35, 517. Achmatowicz, B.; Jankowski, P.; Wicha, J. Tetrahedron Lett. 1996, 37, 5589.
10. Burford, C.; Cooke, F.; Roy, G.; Magnus, P. Tetrahedron 1983, 39, 867. Molander, G. A.; Mautner, K. J. Org. Chem. 1989, 54, 4042. Molander, G. A.; Mautner, K. Pure Appl. Chem. 1990, 62, 707. Murthi, K. K.; Salomon, R. G. Tetrahedron Lett. 1994, 35, 517. Achmatowicz, B.; Jankowski, P.; Wicha, J. Tetrahedron Lett. 1996, 37, 5589.
11. Burford, C.; Cooke, F.; Roy, G.; Magnus, P. Tetrahedron 1983, 39, 867. Molander, G. A.; Mautner, K. J. Org. Chem. 1989, 54, 4042. Molander, G. A.; Mautner, K. Pure Appl. Chem. 1990, 62, 707. Murthi, K. K.; Salomon, R. G. Tetrahedron Lett. 1994, 35, 517. Achmatowicz, B.; Jankowski, P.; Wicha, J. Tetrahedron Lett. 1996, 37, 5589.
12. Burford, C.; Cooke, F.; Roy, G.; Magnus, P. Tetrahedron 1983, 39, 867. Molander, G. A.; Mautner, K. J. Org. Chem. 1989, 54, 4042. Molander, G. A.; Mautner, K. Pure Appl. Chem. 1990, 62, 707. Murthi, K. K.; Salomon, R. G. Tetrahedron Lett. 1994, 35, 517. Achmatowicz, B.; Jankowski, P.; Wicha, J. Tetrahedron Lett. 1996, 37, 5589.
13. Burford, C.; Cooke, F.; Roy, G.; Magnus, P. Tetrahedron 1983, 39, 867. Molander, G. A.; Mautner, K. J. Org. Chem. 1989, 54, 4042. Molander, G. A.; Mautner, K. Pure Appl. Chem. 1990, 62, 707. Murthi, K. K.; Salomon, R. G. Tetrahedron Lett. 1994, 35, 517. Achmatowicz, B.; Jankowski, P.; Wicha, J. Tetrahedron Lett. 1996, 37, 5589.
14. Dubuffet, T; Sauvetre, R.; Normant, J. F. Tetrahedron Lett. 1988, 29, 5923.
15. Eisch, J. J.; Galle, J. E. J. Org. Chem. 1990, 55, 4835. Grandjean, D.; Pale, P.; Chuche, J.Tetrahedron Asymmetry 1993, 4, 1991. Florio, S.; Ingrosso, G.; Troisi, L.; Lucchini, V. Tetrahedron Lett. 1993, 34, 1363.
16. Eisch, J. J.; Galle, J. E. J. Org. Chem. 1990, 55, 4835. Grandjean, D.; Pale, P.; Chuche, J. Tetrahedron Asymmetry 1993, 4, 1991. Florio, S.; Ingrosso, G.; Troisi, L.; Lucchini, V. Tetrahedron Lett. 1993, 34, 1363.
17. Eisch, J. J.; Galle, J. E. J. Org. Chem. 1990, 55, 4835. Grandjean, D.; Pale, P.; Chuche, J.Tetrahedron Asymmetry 1993, 4, 1991. Florio, S.; Ingrosso, G.; Troisi, L.; Lucchini, V. Tetrahedron Lett. 1993, 34, 1363.
18. Ashwell, M.; Jackson, R. F. W. J. Chem. Soc., Chem. Commun. 1988, 645. Ashwell, M.; Clegg,w.; Jackson, R. F. W. J. Chem. Soc., Perkin Trans. I 1991, 897. Hewkin, C. T.; Jackson, R. F. W.; Clegg, W. J. Chem. Soc., Perkin Trans. I 1991, 3091. Dunn, S. F. C.; Jackson, R. F. W. J. Chem. Soc., Perkin Trans. I 1992, 2863.
19. Ashwell, M.; Jackson, R. F. W. J. Chem. Soc., Chem. Commun. 1988, 645. Ashwell, M.; Clegg, W.; Jackson, R. F. W. J. Chem. Soc., Perkin Trans. I 1991, 897. Hewkin, C. T.; Jackson, R. F. W.; Clegg, W. J. Chem. Soc., Perkin Trans. I 1991, 3091. Dunn, S. F. C.; Jackson, R. F. W. J. Chem. Soc., Perkin Trans. I 1992, 2863.
20. Ashwell, M.; Jackson, R. F. W. J. Chem. Soc., Chem. Commun. 1988, 645. Ashwell, M.; Clegg,w.; Jackson, R. F. W. J. Chem. Soc., Perkin Trans. I 1991, 897. Hewkin, C. T.; Jackson, R. F. W.; Clegg, W. J. Chem. Soc., Perkin Trans. I 1991, 3091. Dunn, S. F. C.; Jackson, R. F. W. J. Chem. Soc., Perkin Trans. I 1992, 2863.
21. Ashwell, M.; Jackson, R. F. W. J. Chem. Soc., Chem. Commun. 1988, 645. Ashwell, M.; Clegg,w.; Jackson, R. F. W. J. Chem. Soc., Perkin Trans. I 1991, 897. Hewkin, C. T.; Jackson, R. F. W.; Clegg, W. J. Chem. Soc., Perkin Trans. I 1991, 3091. Dunn, S. F. C.; Jackson, R. F. W. J. Chem. Soc., Perkin Trans. I 1992, 2863.
22. Mori, Y.; Yaegashi, K.; Iwase, K.; Yamamori, Y.; Furukawa, H. Tetrahedron Lett. 1996, 37, 2605. Mori, Y.; Yaegashi, K.; Furukawa, H. J. Am. Chem. Soc. 1996, 118, 8158. Mori, Y.; Yaegashi, K.; Furukawa, H. J. Am. Chem. Soc. 1997, 119, 4557. Mori, Y.; Yaegashi, K.; Furukawa, H. Tetrahedron 1997, 53, 12917. Mori, Y. J. Syn. Org. Chem. Jpn. 1997, 55, 176. Mori, Y.; Yaegashi, K.; Furukawa, H. J. Org. Chem. 1998, 63, 6200.
23. Mori, Y.; Yaegashi, K.; Iwase, K.; Yamamori, Y.; Furukawa, H. Tetrahedron Lett. 1996, 37, 2605. Mori, Y.; Yaegashi, K.; Furukawa, H. J. Am. Chem. Soc. 1996, 118, 8158. Mori, Y.; Yaegashi, K.; Furukawa, H. J. Am. Chem. Soc. 1997, 119, 4557. Mori, Y.; Yaegashi, K.; Furukawa, H. Tetrahedron 1997, 53, 12917. Mori, Y. J. Syn. Org. Chem. Jpn. 1997, 55, 176. Mori, Y.; Yaegashi, K.; Furukawa, H. J. Org. Chem. 1998, 63, 6200.
24. Mori, Y.; Yaegashi, K.; Iwase, K.; Yamamori, Y.; Furukawa, H. Tetrahedron Lett. 1996, 37, 2605. Mori, Y.; Yaegashi, K.; Furukawa, H. J. Am. Chem. Soc. 1996, 118, 8158. Mori, Y.; Yaegashi, K.; Furukawa, H. J. Am. Chem. Soc. 1997, 119, 4557. Mori, Y.; Yaegashi, K.; Furukawa, H. Tetrahedron 1997, 53, 12917. Mori, Y. J. Syn. Org. Chem. Jpn. 1997, 55, 176. Mori, Y.; Yaegashi, K.; Furukawa, H. J. Org. Chem. 1998, 63, 6200.
25. Mori, Y.; Yaegashi, K.; Iwase, K.; Yamamori, Y.; Furukawa, H. Tetrahedron Lett. 1996, 37, 2605. Mori, Y.; Yaegashi, K.; Furukawa, H. J. Am. Chem. Soc. 1996, 118, 8158. Mori, Y.; Yaegashi, K.; Furukawa, H. J. Am. Chem. Soc. 1997, 119, 4557. Mori, Y.; Yaegashi, K.; Furukawa, H. Tetrahedron 1997, 53, 12917. Mori, Y. J. Syn. Org. Chem. Jpn. 1997, 55, 176. Mori, Y.; Yaegashi, K.; Furukawa, H. J. Org. Chem. 1998, 63, 6200.
26. Mori, Y.; Yaegashi, K.; Iwase, K.; Yamamori, Y.; Furukawa, H. Tetrahedron Lett. 1996, 37, 2605. Mori, Y.; Yaegashi, K.; Furukawa, H. J. Am. Chem. Soc. 1996, 118, 8158. Mori, Y.; Yaegashi, K.; Furukawa, H. J. Am. Chem. Soc. 1997, 119, 4557. Mori, Y.; Yaegashi, K.; Furukawa, H. Tetrahedron 1997, 53, 12917. Mori, Y. J. Syn. Org. Chem. Jpn. 1997, 55, 176. Mori, Y.; Yaegashi, K.; Furukawa, H. J. Org. Chem. 1998, 63, 6200.
27. Mori, Y.; Yaegashi, K.; Iwase, K.; Yamamori, Y.; Furukawa, H. Tetrahedron Lett. 1996, 37, 2605. Mori, Y.; Yaegashi, K.; Furukawa, H. J. Am. Chem. Soc. 1996, 118, 8158. Mori, Y.; Yaegashi, K.; Furukawa, H. J. Am. Chem. Soc. 1997, 119, 4557. Mori, Y.; Yaegashi, K.; Furukawa, H. Tetrahedron 1997, 53, 12917. Mori, Y. J. Syn. Org. Chem. Jpn. 1997, 55, 176. Mori, Y.; Yaegashi, K.; Furukawa, H. J. Org. Chem. 1998, 63, 6200.
28. Lohse, P.; Loner, H.; Acklin, P.; Sternfeld, F.; Pfaltz, A. Tetrahedron Lett. 1991, 32, 615.
29. Satoh, T.; Horiguch, K. Tetrahedron Lett. 1995, 36, 8235.
30. Satoh, T. J. Syn. Org. Chem. Jpn. 1996, 54, 481.
31. a) Satoh, T.; Kaneko, Y.; Yamakawa, K. Tetrahedron Lett. 1986, 27, 2379. b) Satoh, T.; Kaneko, Y.; Yamakawa, K. Bull. Chem. Soc. Jpn. 1986, 59, 2463. c) Satoh, T.; Oohara, T.; Ueda, Y.; Yamakawa, K. Tetrahedron Lett. 1988, 29, 313. d) Satoh, T.; Oohara, T.; Yamakawa, K. Tetrahedron Lett. 1988, 29, 2851. e) Satoh, T.; Oohara, T.; Ueda, Y.; Yamakawa, K. J. Org. Chem. 1989, 54, 3130.
32. a) Satoh, T.; Kaneko, Y.; Yamakawa, K. Tetrahedron Lett. 1986, 27, 2379. b) Satoh, T.; Kaneko, Y.; Yamakawa, K. Bull. Chem. Soc. Jpn. 1986, 59, 2463. c) Satoh, T.; Oohara, T.; Ueda, Y.; Yamakawa, K. Tetrahedron Lett. 1988, 29, 313. d) Satoh, T.; Oohara, T.; Yamakawa, K. Tetrahedron Lett. 1988, 29, 2851. e) Satoh, T.; Oohara, T.; Ueda, Y.; Yamakawa, K. J. Org. Chem. 1989, 54, 3130.
33. a) Satoh, T.; Kaneko, Y.; Yamakawa, K. Tetrahedron Lett. 1986, 27, 2379. b) Satoh, T.; Kaneko, Y.; Yamakawa, K. Bull. Chem. Soc. Jpn. 1986, 59, 2463. c) Satoh, T.; Oohara, T.; Ueda, Y.; Yamakawa, K. Tetrahedron Lett. 1988, 29, 313. d) Satoh, T.; Oohara, T.; Yamakawa, K. Tetrahedron Lett. 1988, 29, 2851. e) Satoh, T.; Oohara, T.; Ueda, Y.; Yamakawa, K. J. Org. Chem. 1989, 54, 3130.
34. a) Satoh, T.; Kaneko, Y.; Yamakawa, K. Tetrahedron Lett. 1986, 27, 2379. b) Satoh, T.; Kaneko, Y.; Yamakawa, K. Bull. Chem. Soc. Jpn. 1986, 59, 2463. c) Satoh, T.; Oohara, T.; Ueda, Y.; Yamakawa, K. Tetrahedron Lett. 1988, 29, 313. d) Satoh, T.; Oohara, T.; Yamakawa, K. Tetrahedron Lett. 1988, 29, 2851. e) Satoh, T.; Oohara, T.; Ueda, Y.; Yamakawa, K. J. Org. Chem. 1989, 54, 3130.
35. a) Satoh, T.; Kaneko, Y.; Yamakawa, K. Tetrahedron Lett. 1986, 27, 2379. b) Satoh, T.; Kaneko, Y.; Yamakawa, K. Bull. Chem. Soc. Jpn. 1986, 59, 2463. c) Satoh, T.; Oohara, T.; Ueda, Y.; Yamakawa, K. Tetrahedron Lett. 1988, 29, 313. d) Satoh, T.; Oohara, T.; Yamakawa, K. Tetrahedron Lett. 1988, 29, 2851. e) Satoh, T.; Oohara, T.; Ueda, Y.; Yamakawa, K. J. Org. Chem. 1989, 54, 3130.
36. The sulfinyloxiranes in this paper were synthesized from 1-chloroalkyl p-tolyl sulfoxides and corresponding ketones or aldehydes as described in a previous paper: Satoh, T.; Kumagawa, T.; Sugimoto, A.; Yamakawa, K. Bull. Chem. Soc. Jpn. 1987, 60, 301. Experimental details, see also lit. 13b and 13e. Selected data are reported in experimental section.
37. Satoh, T.; Takano, K. Tetrahedron 1996, 52, 2349.
38. Crandall, J. K.; Lin, L.-H. C. J. Am. Chem. Soc. 1967, 89, 4526. Crandall, J. K.; Lin, L.-H. C. J. Am. Chem. Soc. 1967, 89, 4527.
39. Crandall, J. K.; Lin, L.-H. C. J. Am. Chem. Soc. 1967, 89, 4526. Crandall, J. K.; Lin, L.-H. C. J. Am. Chem. Soc. 1967, 89, 4527.
40. Daicel Chiralpak AD, 10% 2-propanol in hexane, flow rate 0.5 ml/min. The optical purity of (+)-18, (+)-20, and (-)-63 were found to be over 98% ee.