Distannoxane-catalyzed selective acetylation of 3-chloropropane-1,2- diol: A convenient synthesis of enantiopure epichlorohydrin

Synlett

Volumn , Issue 12, 1999, Pages 1927-1929

  Orita, Akihiro ^a   Ito, Toshihide ^a   Yasui, Yutaka ^a   Otera, Junzo ^a  

^a OKAYAMA UNIVERSITY OF SCIENCE   (Japan)

Author keywords

1,2 diol; Acetylation; Distannoxane; Epichlorohydrin

Indexed keywords

ALPHA CHLOROHYDRIN; EPICHLOROHYDRIN;

ACETYLATION; ARTICLE; CATALYSIS; ENANTIOMER; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; SYNTHESIS;

EID: 0032712946     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1999-2991     Document Type: Article

References (26)

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8. For other representative preparations of optically active epichlorohydrin: Takeichi, T.; Arihara, M.; Ishimori, M.; Tsuruta, T. Tetrahedron 1980, 36, 3391. Baldwin, J. J.; Raab, A. W.; Mensler, K.; Arison, B. H.; McLure, D. E. J. Org. Chem. 1978, 43, 4876.
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10. For selective acylation of 1,2-diols: Sekine, M.; Kume, A.; Hata, T. Tetrahedron Lett. 1981, 22, 3617. Kunieda, T.; Mori, T.; Higuchi, T.; Hirobe, M. Tetrahedron Lett. 1985, 26, 1977. Kim, S.; Chang, H.; Kim, W. J. J. Org. Chem. 1985, 50, 1751. Nishiguchi, T.; Taya, H. J. Am. Chem. Soc. 1989, 111, 9102. Yamada, S. J. Org. Chem. 1992, 57, 1591. Ishihara, K.; Kurihara, H.; Yamamoto, H. J. Org. Chem. 1993, 58, 3791. Morcuende, A.; Valverde, S.; Herradón, B. Synlett 1994, 89. Herradón, B.; Morcuende, A.; Valverde, S. Synlett 1995, 455. Oikawa, M.; Wada, A.; Okazaki, F.; Kusumoto, S. J. Org. Chem. 1996, 61, 4469. Maki, T.; Iwasaki, F.; Matsumura, Y. Tetrahedron Lett. 1998, 39, 5601.
11. For selective acylation of 1,2-diols: Sekine, M.; Kume, A.; Hata, T. Tetrahedron Lett. 1981, 22, 3617. Kunieda, T.; Mori, T.; Higuchi, T.; Hirobe, M. Tetrahedron Lett. 1985, 26, 1977. Kim, S.; Chang, H.; Kim, W. J. J. Org. Chem. 1985, 50, 1751. Nishiguchi, T.; Taya, H. J. Am. Chem. Soc. 1989, 111, 9102. Yamada, S. J. Org. Chem. 1992, 57, 1591. Ishihara, K.; Kurihara, H.; Yamamoto, H. J. Org. Chem. 1993, 58, 3791. Morcuende, A.; Valverde, S.; Herradón, B. Synlett 1994, 89. Herradón, B.; Morcuende, A.; Valverde, S. Synlett 1995, 455. Oikawa, M.; Wada, A.; Okazaki, F.; Kusumoto, S. J. Org. Chem. 1996, 61, 4469. Maki, T.; Iwasaki, F.; Matsumura, Y. Tetrahedron Lett. 1998, 39, 5601.
12. For selective acylation of 1,2-diols: Sekine, M.; Kume, A.; Hata, T. Tetrahedron Lett. 1981, 22, 3617. Kunieda, T.; Mori, T.; Higuchi, T.; Hirobe, M. Tetrahedron Lett. 1985, 26, 1977. Kim, S.; Chang, H.; Kim, W. J. J. Org. Chem. 1985, 50, 1751. Nishiguchi, T.; Taya, H. J. Am. Chem. Soc. 1989, 111, 9102. Yamada, S. J. Org. Chem. 1992, 57, 1591. Ishihara, K.; Kurihara, H.; Yamamoto, H. J. Org. Chem. 1993, 58, 3791. Morcuende, A.; Valverde, S.; Herradón, B. Synlett 1994, 89. Herradón, B.; Morcuende, A.; Valverde, S. Synlett 1995, 455. Oikawa, M.; Wada, A.; Okazaki, F.; Kusumoto, S. J. Org. Chem. 1996, 61, 4469. Maki, T.; Iwasaki, F.; Matsumura, Y. Tetrahedron Lett. 1998, 39, 5601.
13. For selective acylation of 1,2-diols: Sekine, M.; Kume, A.; Hata, T. Tetrahedron Lett. 1981, 22, 3617. Kunieda, T.; Mori, T.; Higuchi, T.; Hirobe, M. Tetrahedron Lett. 1985, 26, 1977. Kim, S.; Chang, H.; Kim, W. J. J. Org. Chem. 1985, 50, 1751. Nishiguchi, T.; Taya, H. J. Am. Chem. Soc. 1989, 111, 9102. Yamada, S. J. Org. Chem. 1992, 57, 1591. Ishihara, K.; Kurihara, H.; Yamamoto, H. J. Org. Chem. 1993, 58, 3791. Morcuende, A.; Valverde, S.; Herradón, B. Synlett 1994, 89. Herradón, B.; Morcuende, A.; Valverde, S. Synlett 1995, 455. Oikawa, M.; Wada, A.; Okazaki, F.; Kusumoto, S. J. Org. Chem. 1996, 61, 4469. Maki, T.; Iwasaki, F.; Matsumura, Y. Tetrahedron Lett. 1998, 39, 5601.
14. For selective acylation of 1,2-diols: Sekine, M.; Kume, A.; Hata, T. Tetrahedron Lett. 1981, 22, 3617. Kunieda, T.; Mori, T.; Higuchi, T.; Hirobe, M. Tetrahedron Lett. 1985, 26, 1977. Kim, S.; Chang, H.; Kim, W. J. J. Org. Chem. 1985, 50, 1751. Nishiguchi, T.; Taya, H. J. Am. Chem. Soc. 1989, 111, 9102. Yamada, S. J. Org. Chem. 1992, 57, 1591. Ishihara, K.; Kurihara, H.; Yamamoto, H. J. Org. Chem. 1993, 58, 3791. Morcuende, A.; Valverde, S.; Herradón, B. Synlett 1994, 89. Herradón, B.; Morcuende, A.; Valverde, S. Synlett 1995, 455. Oikawa, M.; Wada, A.; Okazaki, F.; Kusumoto, S. J. Org. Chem. 1996, 61, 4469. Maki, T.; Iwasaki, F.; Matsumura, Y. Tetrahedron Lett. 1998, 39, 5601.
15. For selective acylation of 1,2-diols: Sekine, M.; Kume, A.; Hata, T. Tetrahedron Lett. 1981, 22, 3617. Kunieda, T.; Mori, T.; Higuchi, T.; Hirobe, M. Tetrahedron Lett. 1985, 26, 1977. Kim, S.; Chang, H.; Kim, W. J. J. Org. Chem. 1985, 50, 1751. Nishiguchi, T.; Taya, H. J. Am. Chem. Soc. 1989, 111, 9102. Yamada, S. J. Org. Chem. 1992, 57, 1591. Ishihara, K.; Kurihara, H.; Yamamoto, H. J. Org. Chem. 1993, 58, 3791. Morcuende, A.; Valverde, S.; Herradón, B. Synlett 1994, 89. Herradón, B.; Morcuende, A.; Valverde, S. Synlett 1995, 455. Oikawa, M.; Wada, A.; Okazaki, F.; Kusumoto, S. J. Org. Chem. 1996, 61, 4469. Maki, T.; Iwasaki, F.; Matsumura, Y. Tetrahedron Lett. 1998, 39, 5601.
16. For selective acylation of 1,2-diols: Sekine, M.; Kume, A.; Hata, T. Tetrahedron Lett. 1981, 22, 3617. Kunieda, T.; Mori, T.; Higuchi, T.; Hirobe, M. Tetrahedron Lett. 1985, 26, 1977. Kim, S.; Chang, H.; Kim, W. J. J. Org. Chem. 1985, 50, 1751. Nishiguchi, T.; Taya, H. J. Am. Chem. Soc. 1989, 111, 9102. Yamada, S. J. Org. Chem. 1992, 57, 1591. Ishihara, K.; Kurihara, H.; Yamamoto, H. J. Org. Chem. 1993, 58, 3791. Morcuende, A.; Valverde, S.; Herradón, B. Synlett 1994, 89. Herradón, B.; Morcuende, A.; Valverde, S. Synlett 1995, 455. Oikawa, M.; Wada, A.; Okazaki, F.; Kusumoto, S. J. Org. Chem. 1996, 61, 4469. Maki, T.; Iwasaki, F.; Matsumura, Y. Tetrahedron Lett. 1998, 39, 5601.
17. For selective acylation of 1,2-diols: Sekine, M.; Kume, A.; Hata, T. Tetrahedron Lett. 1981, 22, 3617. Kunieda, T.; Mori, T.; Higuchi, T.; Hirobe, M. Tetrahedron Lett. 1985, 26, 1977. Kim, S.; Chang, H.; Kim, W. J. J. Org. Chem. 1985, 50, 1751. Nishiguchi, T.; Taya, H. J. Am. Chem. Soc. 1989, 111, 9102. Yamada, S. J. Org. Chem. 1992, 57, 1591. Ishihara, K.; Kurihara, H.; Yamamoto, H. J. Org. Chem. 1993, 58, 3791. Morcuende, A.; Valverde, S.; Herradón, B. Synlett 1994, 89. Herradón, B.; Morcuende, A.; Valverde, S. Synlett 1995, 455. Oikawa, M.; Wada, A.; Okazaki, F.; Kusumoto, S. J. Org. Chem. 1996, 61, 4469. Maki, T.; Iwasaki, F.; Matsumura, Y. Tetrahedron Lett. 1998, 39, 5601.
18. For selective acylation of 1,2-diols: Sekine, M.; Kume, A.; Hata, T. Tetrahedron Lett. 1981, 22, 3617. Kunieda, T.; Mori, T.; Higuchi, T.; Hirobe, M. Tetrahedron Lett. 1985, 26, 1977. Kim, S.; Chang, H.; Kim, W. J. J. Org. Chem. 1985, 50, 1751. Nishiguchi, T.; Taya, H. J. Am. Chem. Soc. 1989, 111, 9102. Yamada, S. J. Org. Chem. 1992, 57, 1591. Ishihara, K.; Kurihara, H.; Yamamoto, H. J. Org. Chem. 1993, 58, 3791. Morcuende, A.; Valverde, S.; Herradón, B. Synlett 1994, 89. Herradón, B.; Morcuende, A.; Valverde, S. Synlett 1995, 455. Oikawa, M.; Wada, A.; Okazaki, F.; Kusumoto, S. J. Org. Chem. 1996, 61, 4469. Maki, T.; Iwasaki, F.; Matsumura, Y. Tetrahedron Lett. 1998, 39, 5601.
19. For selective acylation of 1,2-diols: Sekine, M.; Kume, A.; Hata, T. Tetrahedron Lett. 1981, 22, 3617. Kunieda, T.; Mori, T.; Higuchi, T.; Hirobe, M. Tetrahedron Lett. 1985, 26, 1977. Kim, S.; Chang, H.; Kim, W. J. J. Org. Chem. 1985, 50, 1751. Nishiguchi, T.; Taya, H. J. Am. Chem. Soc. 1989, 111, 9102. Yamada, S. J. Org. Chem. 1992, 57, 1591. Ishihara, K.; Kurihara, H.; Yamamoto, H. J. Org. Chem. 1993, 58, 3791. Morcuende, A.; Valverde, S.; Herradón, B. Synlett 1994, 89. Herradón, B.; Morcuende, A.; Valverde, S. Synlett 1995, 455. Oikawa, M.; Wada, A.; Okazaki, F.; Kusumoto, S. J. Org. Chem. 1996, 61, 4469. Maki, T.; Iwasaki, F.; Matsumura, Y. Tetrahedron Lett. 1998, 39, 5601.
20. Otera, J. In Advances in Detailed Reaction Mechanism, Coxon Ed.; JAI Press, Inc.: London, 1994, Vol. 3. P 167.
21. Orita, A.; Mitsutome, A.; Otera, J. J. Org. Chem. 1998, 63, 2420.
22. On the assumption that 5 was derived exclusively from 4 in both cases, the selectivity for 3 and 4 in eq. 1 is taken as ca. 9:1.
23. Ishihara, K.; Kubota, M.; Kurihara, H. Yamamoto, H. J. Am. Chem. Soc. 1995, 117, 4413; J. Org. Chem. 1996, 61, 2963.
24. Ishihara, K.; Kubota, M.; Kurihara, H. Yamamoto, H. J. Am. Chem. Soc. 1995, 117, 4413; J. Org. Chem. 1996, 61, 2963.
25. Procopiou, P. A.; Baugh, S. P. D.; Falck, S, S.; Inglis, G. G. A. J. Org. Chem. 1998, 63, 2342.
26. Kindly supplied by Daiso Co. Ltd.