Enantioselective additive pummerer-type reaction in chiral, non-racemic vinyl sulfoxides induced by O-silylated ketene acetal

Chemical and Pharmaceutical Bulletin

Volumn 44, Issue 5, 1996, Pages 892-894

  Shibata, Norio ^a   Fujimori, Chino ^a   Fujita, Shigekazu ^a   Kita, Yasuyuki ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

additive Pummerer reaction; enantioselective reaction; methyl 4 siloxy 4 sulfenylbutyrate; O methyl O tert butyldimethylsilyl ketene acetal; vinyl sulfoxide

Indexed keywords

4 SILOXY 4 SULFENYLBUTYRIC ACID METHYL ESTER; O METHYL O TERT BUTYLDIMETHYLSILYL KETENE ACETAL; SULFOXIDE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; DRUG SYNTHESIS; ENANTIOMER; RACEMIC MIXTURE; STEREOCHEMISTRY;

EID: 0030009170     PISSN: 00092363     EISSN: None     Source Type: Journal    
DOI: 10.1248/cpb.44.892     Document Type: Article

References (45)

1. a) Pummerer R., Chem. Ber., 42, 2282 (1909); 43, 1401 (1910); b) Horner L., Kaiser P., Justus Liebigs Ann. Chem., 626, 19 (1959); Horner L., ibid., 631, 198 (1960).
2. a) Pummerer R., Chem. Ber., 42, 2282 (1909); 43, 1401 (1910); b) Horner L., Kaiser P., Justus Liebigs Ann. Chem., 626, 19 (1959); Horner L., ibid., 631, 198 (1960).
3. a) Pummerer R., Chem. Ber., 42, 2282 (1909); 43, 1401 (1910); b) Horner L., Kaiser P., Justus Liebigs Ann. Chem., 626, 19 (1959); Horner L., ibid., 631, 198 (1960).
4. a) Pummerer R., Chem. Ber., 42, 2282 (1909); 43, 1401 (1910); b) Horner L., Kaiser P., Justus Liebigs Ann. Chem., 626, 19 (1959); Horner L., ibid., 631, 198 (1960).
5. Reviews, see: a) Durst T., Adv. Org. Chem., 6, 285 (1969); b) Numata T., Oae S., Yuki Gosei Kagaku Kyokai Shi, 35, 726 (1977) [Chem. Abstr., 88, 5639s (1978)]; c) Marino J. P., "Topics in Sulfur Chemistry," Vol. I, ed. by Senning A., George Thieme Publishers, Stuttgart. 1976, p. 1; d) Numata T., Yuki Gosei Kagaku Kyokai Shi, 36, 845 (1978) [Chem. Abstr., 90, 136847x (1979)]; e) Oae S., Numata T., "Isotopes in Organic Chemistry," Vol. 5, ed. by Buncel E., Lee C. C., Elsevier, New York, 1980, Chapter 2; f) Oae S., Numata T., Yoshimura T., "The Chemistry of the Sulphonium Group," ed. by Stirling C. J. M., Patai S., John Wiley & Sons, New York. 1981, Part 2, Chapter 15.
6. Reviews, see: a) Durst T., Adv. Org. Chem., 6, 285 (1969); b) Numata T., Oae S., Yuki Gosei Kagaku Kyokai Shi, 35, 726 (1977) [Chem. Abstr., 88, 5639s (1978)]; c) Marino J. P., "Topics in Sulfur Chemistry," Vol. I, ed. by Senning A., George Thieme Publishers, Stuttgart. 1976, p. 1; d) Numata T., Yuki Gosei Kagaku Kyokai Shi, 36, 845 (1978) [Chem. Abstr., 90, 136847x (1979)]; e) Oae S., Numata T., "Isotopes in Organic Chemistry," Vol. 5, ed. by Buncel E., Lee C. C., Elsevier, New York, 1980, Chapter 2; f) Oae S., Numata T., Yoshimura T., "The Chemistry of the Sulphonium Group," ed. by Stirling C. J. M., Patai S., John Wiley & Sons, New York. 1981, Part 2, Chapter 15.
7. Reviews, see: a) Durst T., Adv. Org. Chem., 6, 285 (1969); b) Numata T., Oae S., Yuki Gosei Kagaku Kyokai Shi, 35, 726 (1977) [Chem. Abstr., 88, 5639s (1978)]; c) Marino J. P., "Topics in Sulfur Chemistry," Vol. I, ed. by Senning A., George Thieme Publishers, Stuttgart. 1976, p. 1; d) Numata T., Yuki Gosei Kagaku Kyokai Shi, 36, 845 (1978) [Chem. Abstr., 90, 136847x (1979)]; e) Oae S., Numata T., "Isotopes in Organic Chemistry," Vol. 5, ed. by Buncel E., Lee C. C., Elsevier, New York, 1980, Chapter 2; f) Oae S., Numata T., Yoshimura T., "The Chemistry of the Sulphonium Group," ed. by Stirling C. J. M., Patai S., John Wiley & Sons, New York. 1981, Part 2, Chapter 15.
8. Reviews, see: a) Durst T., Adv. Org. Chem., 6, 285 (1969); b) Numata T., Oae S., Yuki Gosei Kagaku Kyokai Shi, 35, 726 (1977) [Chem. Abstr., 88, 5639s (1978)]; c) Marino J. P., "Topics in Sulfur Chemistry," Vol. I, ed. by Senning A., George Thieme Publishers, Stuttgart. 1976, p. 1; d) Numata T., Yuki Gosei Kagaku Kyokai Shi, 36, 845 (1978) [Chem. Abstr., 90, 136847x (1979)]; e) Oae S., Numata T., "Isotopes in Organic Chemistry," Vol. 5, ed. by Buncel E., Lee C. C., Elsevier, New York, 1980, Chapter 2; f) Oae S., Numata T., Yoshimura T., "The Chemistry of the Sulphonium Group," ed. by Stirling C. J. M., Patai S., John Wiley & Sons, New York. 1981, Part 2, Chapter 15.
9. Reviews, see: a) Durst T., Adv. Org. Chem., 6, 285 (1969); b) Numata T., Oae S., Yuki Gosei Kagaku Kyokai Shi, 35, 726 (1977) [Chem. Abstr., 88, 5639s (1978)]; c) Marino J. P., "Topics in Sulfur Chemistry," Vol. I, ed. by Senning A., George Thieme Publishers, Stuttgart. 1976, p. 1; d) Numata T., Yuki Gosei Kagaku Kyokai Shi, 36, 845 (1978) [Chem. Abstr., 90, 136847x (1979)]; e) Oae S., Numata T., "Isotopes in Organic Chemistry," Vol. 5, ed. by Buncel E., Lee C. C., Elsevier, New York, 1980, Chapter 2; f) Oae S., Numata T., Yoshimura T., "The Chemistry of the Sulphonium Group," ed. by Stirling C. J. M., Patai S., John Wiley & Sons, New York. 1981, Part 2, Chapter 15.
10. Reviews, see: a) Durst T., Adv. Org. Chem., 6, 285 (1969); b) Numata T., Oae S., Yuki Gosei Kagaku Kyokai Shi, 35, 726 (1977) [Chem. Abstr., 88, 5639s (1978)]; c) Marino J. P., "Topics in Sulfur Chemistry," Vol. I, ed. by Senning A., George Thieme Publishers, Stuttgart. 1976, p. 1; d) Numata T., Yuki Gosei Kagaku Kyokai Shi, 36, 845 (1978) [Chem. Abstr., 90, 136847x (1979)]; e) Oae S., Numata T., "Isotopes in Organic Chemistry," Vol. 5, ed. by Buncel E., Lee C. C., Elsevier, New York, 1980, Chapter 2; f) Oae S., Numata T., Yoshimura T., "The Chemistry of the Sulphonium Group," ed. by Stirling C. J. M., Patai S., John Wiley & Sons, New York. 1981, Part 2, Chapter 15.
11. Reviews, see: a) Durst T., Adv. Org. Chem., 6, 285 (1969); b) Numata T., Oae S., Yuki Gosei Kagaku Kyokai Shi, 35, 726 (1977) [Chem. Abstr., 88, 5639s (1978)]; c) Marino J. P., "Topics in Sulfur Chemistry," Vol. I, ed. by Senning A., George Thieme Publishers, Stuttgart. 1976, p. 1; d) Numata T., Yuki Gosei Kagaku Kyokai Shi, 36, 845 (1978) [Chem. Abstr., 90, 136847x (1979)]; e) Oae S., Numata T., "Isotopes in Organic Chemistry," Vol. 5, ed. by Buncel E., Lee C. C., Elsevier, New York, 1980, Chapter 2; f) Oae S., Numata T., Yoshimura T., "The Chemistry of the Sulphonium Group," ed. by Stirling C. J. M., Patai S., John Wiley & Sons, New York. 1981, Part 2, Chapter 15.
12. Reviews, see: a) Durst T., Adv. Org. Chem., 6, 285 (1969); b) Numata T., Oae S., Yuki Gosei Kagaku Kyokai Shi, 35, 726 (1977) [Chem. Abstr., 88, 5639s (1978)]; c) Marino J. P., "Topics in Sulfur Chemistry," Vol. I, ed. by Senning A., George Thieme Publishers, Stuttgart. 1976, p. 1; d) Numata T., Yuki Gosei Kagaku Kyokai Shi, 36, 845 (1978) [Chem. Abstr., 90, 136847x (1979)]; e) Oae S., Numata T., "Isotopes in Organic Chemistry," Vol. 5, ed. by Buncel E., Lee C. C., Elsevier, New York, 1980, Chapter 2; f) Oae S., Numata T., Yoshimura T., "The Chemistry of the Sulphonium Group," ed. by Stirling C. J. M., Patai S., John Wiley & Sons, New York. 1981, Part 2, Chapter 15.
13. a) Kita Y., Yasuda H., Tamura O., Itoh F., Tamura Y., Tetrahedron Lett., 25, 4681 (1984);
14. b) Kita Y., Yasuda H., Tamura O., Itoh F., Tamura Y., Chem. Pharm. Bull., 33, 4235 (1985);
15. c) Kita Y., Tamura O., Itoh F., Yasuda H., Miki T., Tamura Y., ibid., 35, 562 (1987);
16. d) Kita Y., Shibata N., Yoshida N., Tetrahedron Lett., 34, 4063 (1993);
17. e) Kita Y., Shibata N., Yoshida N., Fujita S., J. Chem. Soc., Perkin Trans. 1, 1994, 3335;
18. f) Kita Y., Shibata N., Fukui S., Fujita S., Tetrahedron Lett., 35, 9733 (1994).
19. For reviews, see: a) Kita Y., Shibata N., Yuki Gosei Kagaku Kyoukai Shi, 52, 746 (1994) [Chem. Ahstr., 121, 229955e (1994)]; b) Kita Y., Shibata N., Synlett, in press.
20. For reviews, see: a) Kita Y., Shibata N., Yuki Gosei Kagaku Kyoukai Shi, 52, 746 (1994) [Chem. Ahstr., 121, 229955e (1994)]; b) Kita Y., Shibata N., Synlett, in press.
21. For reviews, see: a) Kita Y., Shibata N., Yuki Gosei Kagaku Kyoukai Shi, 52, 746 (1994) [Chem. Ahstr., 121, 229955e (1994)]; b) Kita Y., Shibata N., Synlett, in press.
22. Kita Y., Shibata N., Yoshida N., Fukui S., Fujimori C., Tetrahedron Lett., 35, 2569 (1994); Kita Y., Shibata N., Yoshida N., Kawano N., Fujimori C., Yoshikawa N., Fujita S., J. Chem. Soc., Perkin Trans. 1, 1995, 2829.
23. Kita Y., Shibata N., Yoshida N., Fukui S., Fujimori C., Tetrahedron Lett., 35, 2569 (1994); Kita Y., Shibata N., Yoshida N., Kawano N., Fujimori C., Yoshikawa N., Fujita S., J. Chem. Soc., Perkin Trans. 1, 1995, 2829.
24. For a review, see: Block E., "Reaction of Organosulfur Compounds," Academic Press, New York, 1980; Kosugi H., Yuki Gousei Kagaku Kyokai Shi, 45, 472 (1987) [Chem. Abstr., 107, 133573p (1987)]; a) Yamagiwa S., Sato H., Hoshi N., Kosugi H., Uda H., J. Chem. Soc., Perkin Trans. 1, 1979, 570; b) Marino J. P., Neisser M., J. Am. Chem. Soc., 103, 7687 (1981); Marino J. P., Perez A. D., ibid., 106, 7643 (1984); Marino J. P., Pradilla R. F., Tetrahedron Lett., 26, 5381 (1985); c) Lucchi D., Marchioro G., Modena G., J. Chem. Soc., Chem. Commun., 1984, 513; d) Binns M. R., Chai O. L., Haynes R. K., Katsifis A. A., Schober P. A., Vonwiller S. C., Tetrahedron Lett., 26, 1569 (1985); e) Craig D., Daniels K., Mackenzie A. R., ibid., 32, 6973 (1991); f) Iwata C., Maezaki N., Kurumada T., Fukuyama H., Sugiyama K., Imanishi T., J. Chem. Soc., Chem. Commun., 1991, 1408; g) Trofimov B. A., Chernysheva N. A., Khil'ko M. Ya., Gusarova N. K., Izv. Akad. Nauk SSSR, Ser. Khim., 1991, 2162 [Chem. Abstr., 116, 6128h (1992)]; Trofimov B. A., Gusarova N. K., Chernysheva N. A., Khil'ko M. Ya., Sulfur Lett., 13, 175 (1991); h) Brichard M.-H., Janousek Z., Merényi R., Viehe H. G., Tetrahedron Lett., 33, 2511 (1992); Harvery J., Brichard M.-H., Viehe H. G., J. Chem. Soc., Perkin Trans. 1, 1993, 2275.
25. For a review, see: Block E., "Reaction of Organosulfur Compounds," Academic Press, New York, 1980; Kosugi H., Yuki Gousei Kagaku Kyokai Shi, 45, 472 (1987) [Chem. Abstr., 107, 133573p (1987)]; a) Yamagiwa S., Sato H., Hoshi N., Kosugi H., Uda H., J. Chem. Soc., Perkin Trans. 1, 1979, 570; b) Marino J. P., Neisser M., J. Am. Chem. Soc., 103, 7687 (1981); Marino J. P., Perez A. D., ibid., 106, 7643 (1984); Marino J. P., Pradilla R. F., Tetrahedron Lett., 26, 5381 (1985); c) Lucchi D., Marchioro G., Modena G., J. Chem. Soc., Chem. Commun., 1984, 513; d) Binns M. R., Chai O. L., Haynes R. K., Katsifis A. A., Schober P. A., Vonwiller S. C., Tetrahedron Lett., 26, 1569 (1985); e) Craig D., Daniels K., Mackenzie A. R., ibid., 32, 6973 (1991); f) Iwata C., Maezaki N., Kurumada T., Fukuyama H., Sugiyama K., Imanishi T., J. Chem. Soc., Chem. Commun., 1991, 1408; g) Trofimov B. A., Chernysheva N. A., Khil'ko M. Ya., Gusarova N. K., Izv. Akad. Nauk SSSR, Ser. Khim., 1991, 2162 [Chem. Abstr., 116, 6128h (1992)]; Trofimov B. A., Gusarova N. K., Chernysheva N. A., Khil'ko M. Ya., Sulfur Lett., 13, 175 (1991); h) Brichard M.-H., Janousek Z., Merényi R., Viehe H. G., Tetrahedron Lett., 33, 2511 (1992); Harvery J., Brichard M.-H., Viehe H. G., J. Chem. Soc., Perkin Trans. 1, 1993, 2275.
26. For a review, see: Block E., "Reaction of Organosulfur Compounds," Academic Press, New York, 1980; Kosugi H., Yuki Gousei Kagaku Kyokai Shi, 45, 472 (1987) [Chem. Abstr., 107, 133573p (1987)]; a) Yamagiwa S., Sato H., Hoshi N., Kosugi H., Uda H., J. Chem. Soc., Perkin Trans. 1, 1979, 570; b) Marino J. P., Neisser M., J. Am. Chem. Soc., 103, 7687 (1981); Marino J. P., Perez A. D., ibid., 106, 7643 (1984); Marino J. P., Pradilla R. F., Tetrahedron Lett., 26, 5381 (1985); c) Lucchi D., Marchioro G., Modena G., J. Chem. Soc., Chem. Commun., 1984, 513; d) Binns M. R., Chai O. L., Haynes R. K., Katsifis A. A., Schober P. A., Vonwiller S. C., Tetrahedron Lett., 26, 1569 (1985); e) Craig D., Daniels K., Mackenzie A. R., ibid., 32, 6973 (1991); f) Iwata C., Maezaki N., Kurumada T., Fukuyama H., Sugiyama K., Imanishi T., J. Chem. Soc., Chem. Commun., 1991, 1408; g) Trofimov B. A., Chernysheva N. A., Khil'ko M. Ya., Gusarova N. K., Izv. Akad. Nauk SSSR, Ser. Khim., 1991, 2162 [Chem. Abstr., 116, 6128h (1992)]; Trofimov B. A., Gusarova N. K., Chernysheva N. A., Khil'ko M. Ya., Sulfur Lett., 13, 175 (1991); h) Brichard M.-H., Janousek Z., Merényi R., Viehe H. G., Tetrahedron Lett., 33, 2511 (1992); Harvery J., Brichard M.-H., Viehe H. G., J. Chem. Soc., Perkin Trans. 1, 1993, 2275.
27. For a review, see: Block E., "Reaction of Organosulfur Compounds," Academic Press, New York, 1980; Kosugi H., Yuki Gousei Kagaku Kyokai Shi, 45, 472 (1987) [Chem. Abstr., 107, 133573p (1987)]; a) Yamagiwa S., Sato H., Hoshi N., Kosugi H., Uda H., J. Chem. Soc., Perkin Trans. 1, 1979, 570; b) Marino J. P., Neisser M., J. Am. Chem. Soc., 103, 7687 (1981); Marino J. P., Perez A. D., ibid., 106, 7643 (1984); Marino J. P., Pradilla R. F., Tetrahedron Lett., 26, 5381 (1985); c) Lucchi D., Marchioro G., Modena G., J. Chem. Soc., Chem. Commun., 1984, 513; d) Binns M. R., Chai O. L., Haynes R. K., Katsifis A. A., Schober P. A., Vonwiller S. C., Tetrahedron Lett., 26, 1569 (1985); e) Craig D., Daniels K., Mackenzie A. R., ibid., 32, 6973 (1991); f) Iwata C., Maezaki N., Kurumada T., Fukuyama H., Sugiyama K., Imanishi T., J. Chem. Soc., Chem. Commun., 1991, 1408; g) Trofimov B. A., Chernysheva N. A., Khil'ko M. Ya., Gusarova N. K., Izv. Akad. Nauk SSSR, Ser. Khim., 1991, 2162 [Chem. Abstr., 116, 6128h (1992)]; Trofimov B. A., Gusarova N. K., Chernysheva N. A., Khil'ko M. Ya., Sulfur Lett., 13, 175 (1991); h) Brichard M.-H., Janousek Z., Merényi R., Viehe H. G., Tetrahedron Lett., 33, 2511 (1992); Harvery J., Brichard M.-H., Viehe H. G., J. Chem. Soc., Perkin Trans. 1, 1993, 2275.
28. For a review, see: Block E., "Reaction of Organosulfur Compounds," Academic Press, New York, 1980; Kosugi H., Yuki Gousei Kagaku Kyokai Shi, 45, 472 (1987) [Chem. Abstr., 107, 133573p (1987)]; a) Yamagiwa S., Sato H., Hoshi N., Kosugi H., Uda H., J. Chem. Soc., Perkin Trans. 1, 1979, 570; b) Marino J. P., Neisser M., J. Am. Chem. Soc., 103, 7687 (1981); Marino J. P., Perez A. D., ibid., 106, 7643 (1984); Marino J. P., Pradilla R. F., Tetrahedron Lett., 26, 5381 (1985); c) Lucchi D., Marchioro G., Modena G., J. Chem. Soc., Chem. Commun., 1984, 513; d) Binns M. R., Chai O. L., Haynes R. K., Katsifis A. A., Schober P. A., Vonwiller S. C., Tetrahedron Lett., 26, 1569 (1985); e) Craig D., Daniels K., Mackenzie A. R., ibid., 32, 6973 (1991); f) Iwata C., Maezaki N., Kurumada T., Fukuyama H., Sugiyama K., Imanishi T., J. Chem. Soc., Chem. Commun., 1991, 1408; g) Trofimov B. A., Chernysheva N. A., Khil'ko M. Ya., Gusarova N. K., Izv. Akad. Nauk SSSR, Ser. Khim., 1991, 2162 [Chem. Abstr., 116, 6128h (1992)]; Trofimov B. A., Gusarova N. K., Chernysheva N. A., Khil'ko M. Ya., Sulfur Lett., 13, 175 (1991); h) Brichard M.-H., Janousek Z., Merényi R., Viehe H. G., Tetrahedron Lett., 33, 2511 (1992); Harvery J., Brichard M.-H., Viehe H. G., J. Chem. Soc., Perkin Trans. 1, 1993, 2275.
29. For a review, see: Block E., "Reaction of Organosulfur Compounds," Academic Press, New York, 1980; Kosugi H., Yuki Gousei Kagaku Kyokai Shi, 45, 472 (1987) [Chem. Abstr., 107, 133573p (1987)]; a) Yamagiwa S., Sato H., Hoshi N., Kosugi H., Uda H., J. Chem. Soc., Perkin Trans. 1, 1979, 570; b) Marino J. P., Neisser M., J. Am. Chem. Soc., 103, 7687 (1981); Marino J. P., Perez A. D., ibid., 106, 7643 (1984); Marino J. P., Pradilla R. F., Tetrahedron Lett., 26, 5381 (1985); c) Lucchi D., Marchioro G., Modena G., J. Chem. Soc., Chem. Commun., 1984, 513; d) Binns M. R., Chai O. L., Haynes R. K., Katsifis A. A., Schober P. A., Vonwiller S. C., Tetrahedron Lett., 26, 1569 (1985); e) Craig D., Daniels K., Mackenzie A. R., ibid., 32, 6973 (1991); f) Iwata C., Maezaki N., Kurumada T., Fukuyama H., Sugiyama K., Imanishi T., J. Chem. Soc., Chem. Commun., 1991, 1408; g) Trofimov B. A., Chernysheva N. A., Khil'ko M. Ya., Gusarova N. K., Izv. Akad. Nauk SSSR, Ser. Khim., 1991, 2162 [Chem. Abstr., 116, 6128h (1992)]; Trofimov B. A., Gusarova N. K., Chernysheva N. A., Khil'ko M. Ya., Sulfur Lett., 13, 175 (1991); h) Brichard M.-H., Janousek Z., Merényi R., Viehe H. G., Tetrahedron Lett., 33, 2511 (1992); Harvery J., Brichard M.-H., Viehe H. G., J. Chem. Soc., Perkin Trans. 1, 1993, 2275.
30. For a review, see: Block E., "Reaction of Organosulfur Compounds," Academic Press, New York, 1980; Kosugi H., Yuki Gousei Kagaku Kyokai Shi, 45, 472 (1987) [Chem. Abstr., 107, 133573p (1987)]; a) Yamagiwa S., Sato H., Hoshi N., Kosugi H., Uda H., J. Chem. Soc., Perkin Trans. 1, 1979, 570; b) Marino J. P., Neisser M., J. Am. Chem. Soc., 103, 7687 (1981); Marino J. P., Perez A. D., ibid., 106, 7643 (1984); Marino J. P., Pradilla R. F., Tetrahedron Lett., 26, 5381 (1985); c) Lucchi D., Marchioro G., Modena G., J. Chem. Soc., Chem. Commun., 1984, 513; d) Binns M. R., Chai O. L., Haynes R. K., Katsifis A. A., Schober P. A., Vonwiller S. C., Tetrahedron Lett., 26, 1569 (1985); e) Craig D., Daniels K., Mackenzie A. R., ibid., 32, 6973 (1991); f) Iwata C., Maezaki N., Kurumada T., Fukuyama H., Sugiyama K., Imanishi T., J. Chem. Soc., Chem. Commun., 1991, 1408; g) Trofimov B. A., Chernysheva N. A., Khil'ko M. Ya., Gusarova N. K., Izv. Akad. Nauk SSSR, Ser. Khim., 1991, 2162 [Chem. Abstr., 116, 6128h (1992)]; Trofimov B. A., Gusarova N. K., Chernysheva N. A., Khil'ko M. Ya., Sulfur Lett., 13, 175 (1991); h) Brichard M.-H., Janousek Z., Merényi R., Viehe H. G., Tetrahedron Lett., 33, 2511 (1992); Harvery J., Brichard M.-H., Viehe H. G., J. Chem. Soc., Perkin Trans. 1, 1993, 2275.
31. For a review, see: Block E., "Reaction of Organosulfur Compounds," Academic Press, New York, 1980; Kosugi H., Yuki Gousei Kagaku Kyokai Shi, 45, 472 (1987) [Chem. Abstr., 107, 133573p (1987)]; a) Yamagiwa S., Sato H., Hoshi N., Kosugi H., Uda H., J. Chem. Soc., Perkin Trans. 1, 1979, 570; b) Marino J. P., Neisser M., J. Am. Chem. Soc., 103, 7687 (1981); Marino J. P., Perez A. D., ibid., 106, 7643 (1984); Marino J. P., Pradilla R. F., Tetrahedron Lett., 26, 5381 (1985); c) Lucchi D., Marchioro G., Modena G., J. Chem. Soc., Chem. Commun., 1984, 513; d) Binns M. R., Chai O. L., Haynes R. K., Katsifis A. A., Schober P. A., Vonwiller S. C., Tetrahedron Lett., 26, 1569 (1985); e) Craig D., Daniels K., Mackenzie A. R., ibid., 32, 6973 (1991); f) Iwata C., Maezaki N., Kurumada T., Fukuyama H., Sugiyama K., Imanishi T., J. Chem. Soc., Chem. Commun., 1991, 1408; g) Trofimov B. A., Chernysheva N. A., Khil'ko M. Ya., Gusarova N. K., Izv. Akad. Nauk SSSR, Ser. Khim., 1991, 2162 [Chem. Abstr., 116, 6128h (1992)]; Trofimov B. A., Gusarova N. K., Chernysheva N. A., Khil'ko M. Ya., Sulfur Lett., 13, 175 (1991); h) Brichard M.-H., Janousek Z., Merényi R., Viehe H. G., Tetrahedron Lett., 33, 2511 (1992); Harvery J., Brichard M.-H., Viehe H. G., J. Chem. Soc., Perkin Trans. 1, 1993, 2275.
32. For a review, see: Block E., "Reaction of Organosulfur Compounds," Academic Press, New York, 1980; Kosugi H., Yuki Gousei Kagaku Kyokai Shi, 45, 472 (1987) [Chem. Abstr., 107, 133573p (1987)]; a) Yamagiwa S., Sato H., Hoshi N., Kosugi H., Uda H., J. Chem. Soc., Perkin Trans. 1, 1979, 570; b) Marino J. P., Neisser M., J. Am. Chem. Soc., 103, 7687 (1981); Marino J. P., Perez A. D., ibid., 106, 7643 (1984); Marino J. P., Pradilla R. F., Tetrahedron Lett., 26, 5381 (1985); c) Lucchi D., Marchioro G., Modena G., J. Chem. Soc., Chem. Commun., 1984, 513; d) Binns M. R., Chai O. L., Haynes R. K., Katsifis A. A., Schober P. A., Vonwiller S. C., Tetrahedron Lett., 26, 1569 (1985); e) Craig D., Daniels K., Mackenzie A. R., ibid., 32, 6973 (1991); f) Iwata C., Maezaki N., Kurumada T., Fukuyama H., Sugiyama K., Imanishi T., J. Chem. Soc., Chem. Commun., 1991, 1408; g) Trofimov B. A., Chernysheva N. A., Khil'ko M. Ya., Gusarova N. K., Izv. Akad. Nauk SSSR, Ser. Khim., 1991, 2162 [Chem. Abstr., 116, 6128h (1992)]; Trofimov B. A., Gusarova N. K., Chernysheva N. A., Khil'ko M. Ya., Sulfur Lett., 13, 175 (1991); h) Brichard M.-H., Janousek Z., Merényi R., Viehe H. G., Tetrahedron Lett., 33, 2511 (1992); Harvery J., Brichard M.-H., Viehe H. G., J. Chem. Soc., Perkin Trans. 1, 1993, 2275.
33. For a review, see: Block E., "Reaction of Organosulfur Compounds," Academic Press, New York, 1980; Kosugi H., Yuki Gousei Kagaku Kyokai Shi, 45, 472 (1987) [Chem. Abstr., 107, 133573p (1987)]; a) Yamagiwa S., Sato H., Hoshi N., Kosugi H., Uda H., J. Chem. Soc., Perkin Trans. 1, 1979, 570; b) Marino J. P., Neisser M., J. Am. Chem. Soc., 103, 7687 (1981); Marino J. P., Perez A. D., ibid., 106, 7643 (1984); Marino J. P., Pradilla R. F., Tetrahedron Lett., 26, 5381 (1985); c) Lucchi D., Marchioro G., Modena G., J. Chem. Soc., Chem. Commun., 1984, 513; d) Binns M. R., Chai O. L., Haynes R. K., Katsifis A. A., Schober P. A., Vonwiller S. C., Tetrahedron Lett., 26, 1569 (1985); e) Craig D., Daniels K., Mackenzie A. R., ibid., 32, 6973 (1991); f) Iwata C., Maezaki N., Kurumada T., Fukuyama H., Sugiyama K., Imanishi T., J. Chem. Soc., Chem. Commun., 1991, 1408; g) Trofimov B. A., Chernysheva N. A., Khil'ko M. Ya., Gusarova N. K., Izv. Akad. Nauk SSSR, Ser. Khim., 1991, 2162 [Chem. Abstr., 116, 6128h (1992)]; Trofimov B. A., Gusarova N. K., Chernysheva N. A., Khil'ko M. Ya., Sulfur Lett., 13, 175 (1991); h) Brichard M.-H., Janousek Z., Merényi R., Viehe H. G., Tetrahedron Lett., 33, 2511 (1992); Harvery J., Brichard M.-H., Viehe H. G., J. Chem. Soc., Perkin Trans. 1, 1993, 2275.
34. For a review, see: Block E., "Reaction of Organosulfur Compounds," Academic Press, New York, 1980; Kosugi H., Yuki Gousei Kagaku Kyokai Shi, 45, 472 (1987) [Chem. Abstr., 107, 133573p (1987)]; a) Yamagiwa S., Sato H., Hoshi N., Kosugi H., Uda H., J. Chem. Soc., Perkin Trans. 1, 1979, 570; b) Marino J. P., Neisser M., J. Am. Chem. Soc., 103, 7687 (1981); Marino J. P., Perez A. D., ibid., 106, 7643 (1984); Marino J. P., Pradilla R. F., Tetrahedron Lett., 26, 5381 (1985); c) Lucchi D., Marchioro G., Modena G., J. Chem. Soc., Chem. Commun., 1984, 513; d) Binns M. R., Chai O. L., Haynes R. K., Katsifis A. A., Schober P. A., Vonwiller S. C., Tetrahedron Lett., 26, 1569 (1985); e) Craig D., Daniels K., Mackenzie A. R., ibid., 32, 6973 (1991); f) Iwata C., Maezaki N., Kurumada T., Fukuyama H., Sugiyama K., Imanishi T., J. Chem. Soc., Chem. Commun., 1991, 1408; g) Trofimov B. A., Chernysheva N. A., Khil'ko M. Ya., Gusarova N. K., Izv. Akad. Nauk SSSR, Ser. Khim., 1991, 2162 [Chem. Abstr., 116, 6128h (1992)]; Trofimov B. A., Gusarova N. K., Chernysheva N. A., Khil'ko M. Ya., Sulfur Lett., 13, 175 (1991); h) Brichard M.-H., Janousek Z., Merényi R., Viehe H. G., Tetrahedron Lett., 33, 2511 (1992); Harvery J., Brichard M.-H., Viehe H. G., J. Chem. Soc., Perkin Trans. 1, 1993, 2275.
35. For a review, see: Block E., "Reaction of Organosulfur Compounds," Academic Press, New York, 1980; Kosugi H., Yuki Gousei Kagaku Kyokai Shi, 45, 472 (1987) [Chem. Abstr., 107, 133573p (1987)]; a) Yamagiwa S., Sato H., Hoshi N., Kosugi H., Uda H., J. Chem. Soc., Perkin Trans. 1, 1979, 570; b) Marino J. P., Neisser M., J. Am. Chem. Soc., 103, 7687 (1981); Marino J. P., Perez A. D., ibid., 106, 7643 (1984); Marino J. P., Pradilla R. F., Tetrahedron Lett., 26, 5381 (1985); c) Lucchi D., Marchioro G., Modena G., J. Chem. Soc., Chem. Commun., 1984, 513; d) Binns M. R., Chai O. L., Haynes R. K., Katsifis A. A., Schober P. A., Vonwiller S. C., Tetrahedron Lett., 26, 1569 (1985); e) Craig D., Daniels K., Mackenzie A. R., ibid., 32, 6973 (1991); f) Iwata C., Maezaki N., Kurumada T., Fukuyama H., Sugiyama K., Imanishi T., J. Chem. Soc., Chem. Commun., 1991, 1408; g) Trofimov B. A., Chernysheva N. A., Khil'ko M. Ya., Gusarova N. K., Izv. Akad. Nauk SSSR, Ser. Khim., 1991, 2162 [Chem. Abstr., 116, 6128h (1992)]; Trofimov B. A., Gusarova N. K., Chernysheva N. A., Khil'ko M. Ya., Sulfur Lett., 13, 175 (1991); h) Brichard M.-H., Janousek Z., Merényi R., Viehe H. G., Tetrahedron Lett., 33, 2511 (1992); Harvery J., Brichard M.-H., Viehe H. G., J. Chem. Soc., Perkin Trans. 1, 1993, 2275.
36. For a review, see: Block E., "Reaction of Organosulfur Compounds," Academic Press, New York, 1980; Kosugi H., Yuki Gousei Kagaku Kyokai Shi, 45, 472 (1987) [Chem. Abstr., 107, 133573p (1987)]; a) Yamagiwa S., Sato H., Hoshi N., Kosugi H., Uda H., J. Chem. Soc., Perkin Trans. 1, 1979, 570; b) Marino J. P., Neisser M., J. Am. Chem. Soc., 103, 7687 (1981); Marino J. P., Perez A. D., ibid., 106, 7643 (1984); Marino J. P., Pradilla R. F., Tetrahedron Lett., 26, 5381 (1985); c) Lucchi D., Marchioro G., Modena G., J. Chem. Soc., Chem. Commun., 1984, 513; d) Binns M. R., Chai O. L., Haynes R. K., Katsifis A. A., Schober P. A., Vonwiller S. C., Tetrahedron Lett., 26, 1569 (1985); e) Craig D., Daniels K., Mackenzie A. R., ibid., 32, 6973 (1991); f) Iwata C., Maezaki N., Kurumada T., Fukuyama H., Sugiyama K., Imanishi T., J. Chem. Soc., Chem. Commun., 1991, 1408; g) Trofimov B. A., Chernysheva N. A., Khil'ko M. Ya., Gusarova N. K., Izv. Akad. Nauk SSSR, Ser. Khim., 1991, 2162 [Chem. Abstr., 116, 6128h (1992)]; Trofimov B. A., Gusarova N. K., Chernysheva N. A., Khil'ko M. Ya., Sulfur Lett., 13, 175 (1991); h) Brichard M.-H., Janousek Z., Merényi R., Viehe H. G., Tetrahedron Lett., 33, 2511 (1992); Harvery J., Brichard M.-H., Viehe H. G., J. Chem. Soc., Perkin Trans. 1, 1993, 2275.
37. For a review, see: Block E., "Reaction of Organosulfur Compounds," Academic Press, New York, 1980; Kosugi H., Yuki Gousei Kagaku Kyokai Shi, 45, 472 (1987) [Chem. Abstr., 107, 133573p (1987)]; a) Yamagiwa S., Sato H., Hoshi N., Kosugi H., Uda H., J. Chem. Soc., Perkin Trans. 1, 1979, 570; b) Marino J. P., Neisser M., J. Am. Chem. Soc., 103, 7687 (1981); Marino J. P., Perez A. D., ibid., 106, 7643 (1984); Marino J. P., Pradilla R. F., Tetrahedron Lett., 26, 5381 (1985); c) Lucchi D., Marchioro G., Modena G., J. Chem. Soc., Chem. Commun., 1984, 513; d) Binns M. R., Chai O. L., Haynes R. K., Katsifis A. A., Schober P. A., Vonwiller S. C., Tetrahedron Lett., 26, 1569 (1985); e) Craig D., Daniels K., Mackenzie A. R., ibid., 32, 6973 (1991); f) Iwata C., Maezaki N., Kurumada T., Fukuyama H., Sugiyama K., Imanishi T., J. Chem. Soc., Chem. Commun., 1991, 1408; g) Trofimov B. A., Chernysheva N. A., Khil'ko M. Ya., Gusarova N. K., Izv. Akad. Nauk SSSR, Ser. Khim., 1991, 2162 [Chem. Abstr., 116, 6128h (1992)]; Trofimov B. A., Gusarova N. K., Chernysheva N. A., Khil'ko M. Ya., Sulfur Lett., 13, 175 (1991); h) Brichard M.-H., Janousek Z., Merényi R., Viehe H. G., Tetrahedron Lett., 33, 2511 (1992); Harvery J., Brichard M.-H., Viehe H. G., J. Chem. Soc., Perkin Trans. 1, 1993, 2275.
38. For a review, see: Block E., "Reaction of Organosulfur Compounds," Academic Press, New York, 1980; Kosugi H., Yuki Gousei Kagaku Kyokai Shi, 45, 472 (1987) [Chem. Abstr., 107, 133573p (1987)]; a) Yamagiwa S., Sato H., Hoshi N., Kosugi H., Uda H., J. Chem. Soc., Perkin Trans. 1, 1979, 570; b) Marino J. P., Neisser M., J. Am. Chem. Soc., 103, 7687 (1981); Marino J. P., Perez A. D., ibid., 106, 7643 (1984); Marino J. P., Pradilla R. F., Tetrahedron Lett., 26, 5381 (1985); c) Lucchi D., Marchioro G., Modena G., J. Chem. Soc., Chem. Commun., 1984, 513; d) Binns M. R., Chai O. L., Haynes R. K., Katsifis A. A., Schober P. A., Vonwiller S. C., Tetrahedron Lett., 26, 1569 (1985); e) Craig D., Daniels K., Mackenzie A. R., ibid., 32, 6973 (1991); f) Iwata C., Maezaki N., Kurumada T., Fukuyama H., Sugiyama K., Imanishi T., J. Chem. Soc., Chem. Commun., 1991, 1408; g) Trofimov B. A., Chernysheva N. A., Khil'ko M. Ya., Gusarova N. K., Izv. Akad. Nauk SSSR, Ser. Khim., 1991, 2162 [Chem. Abstr., 116, 6128h (1992)]; Trofimov B. A., Gusarova N. K., Chernysheva N. A., Khil'ko M. Ya., Sulfur Lett., 13, 175 (1991); h) Brichard M.-H., Janousek Z., Merényi R., Viehe H. G., Tetrahedron Lett., 33, 2511 (1992); Harvery J., Brichard M.-H., Viehe H. G., J. Chem. Soc., Perkin Trans. 1, 1993, 2275.
39. For a review, see: Block E., "Reaction of Organosulfur Compounds," Academic Press, New York, 1980; Kosugi H., Yuki Gousei Kagaku Kyokai Shi, 45, 472 (1987) [Chem. Abstr., 107, 133573p (1987)]; a) Yamagiwa S., Sato H., Hoshi N., Kosugi H., Uda H., J. Chem. Soc., Perkin Trans. 1, 1979, 570; b) Marino J. P., Neisser M., J. Am. Chem. Soc., 103, 7687 (1981); Marino J. P., Perez A. D., ibid., 106, 7643 (1984); Marino J. P., Pradilla R. F., Tetrahedron Lett., 26, 5381 (1985); c) Lucchi D., Marchioro G., Modena G., J. Chem. Soc., Chem. Commun., 1984, 513; d) Binns M. R., Chai O. L., Haynes R. K., Katsifis A. A., Schober P. A., Vonwiller S. C., Tetrahedron Lett., 26, 1569 (1985); e) Craig D., Daniels K., Mackenzie A. R., ibid., 32, 6973 (1991); f) Iwata C., Maezaki N., Kurumada T., Fukuyama H., Sugiyama K., Imanishi T., J. Chem. Soc., Chem. Commun., 1991, 1408; g) Trofimov B. A., Chernysheva N. A., Khil'ko M. Ya., Gusarova N. K., Izv. Akad. Nauk SSSR, Ser. Khim., 1991, 2162 [Chem. Abstr., 116, 6128h (1992)]; Trofimov B. A., Gusarova N. K., Chernysheva N. A., Khil'ko M. Ya., Sulfur Lett., 13, 175 (1991); h) Brichard M.-H., Janousek Z., Merényi R., Viehe H. G., Tetrahedron Lett., 33, 2511 (1992); Harvery J., Brichard M.-H., Viehe H. G., J. Chem. Soc., Perkin Trans. 1, 1993, 2275.
40. Kita Y., Tamura O., Itoh F., Yasuda H.,. Miki T., Tamura Y., Chem. Pharm. Bull., 35, 562 (1987).
41. Kita Y., Shibata N., Kawano N., Tohjo T., Fujimori C., Matsumoto K., Tetrahedron Lett., 36, 115 (1995); Kita Y., Shibata N., Kawano N., Tohjo T., Fujimori C., Matsumoto K., Fujita S., J. Chem. Soc., Perkin Trans. 1, 1995, 2829.
42. Kita Y., Shibata N., Kawano N., Tohjo T., Fujimori C., Matsumoto K., Tetrahedron Lett., 36, 115 (1995); Kita Y., Shibata N., Kawano N., Tohjo T., Fujimori C., Matsumoto K., Fujita S., J. Chem. Soc., Perkin Trans. 1, 1995, 2829.
43. Kosugi H., Kitaoka M., Tagami K., Uda H., J. Org. Chem., 52, 1078 (1987).
44. Rebiere F., Samuel O., Ricard L., Kagan H. B., J. Org. Chem., 56, 5991 (1991).
45. Mikolajczyk M., Midura W., Grzejszczak S., Zatorski A., Chefezynska A., J. Org. Chem., 43, 473 (1978).