Zinc metal-promoted stereoselective olefination of aldehydes and ketones with gem-dichloro compounds in the presence of chlorotrimethylsilane

Bulletin of the Chemical Society of Japan

Volumn 71, Issue 11, 1998, Pages 2669-2672

  Ishino, Yoshio ^a   Mihara, Masatoshi ^a   Nishihama, Shintaro ^a   Nishiguchi, Ikuzou ^a,b  

^a OSAKA MUNICIPAL TECHNICAL RESEARCH INSTITUTE   (Japan)

^b NAGAOKA UNIVERSITY OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ACRYLIC ACID METHYL ESTER; BENZYLIDENE DICHLORIDE; CHLOROTRIMETHYLSILANE; METHYL DICHLOROACETATE; UNCLASSIFIED DRUG; ZINC COMPLEX;

ARTICLE; BINDING KINETICS; CHEMICAL REACTION KINETICS; ISOLATION PROCEDURE; ISOMERISM; METAL BINDING; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0031733702     PISSN: 00092673     EISSN: None     Source Type: Journal    
DOI: 10.1246/bcsj.71.2669     Document Type: Article

References (25)

1. B. M. Trost, "Comprehensive Organic Synthesis," ed by S. E. Kelly, Pergamon Press, New York (1991), Vol. 1, p. 729; B. E. Maryanoff and A. B. Reitz, Chem. Rev., 89, 863 (1989); L. Fitjer and U. Quabeck, Synth. Commun., 15, 855 (1985); A. R. Katritzky and J. Li, J. Org. Chem., 62, 238 (1997).
2. B. M. Trost, "Comprehensive Organic Synthesis," ed by S. E. Kelly, Pergamon Press, New York (1991), Vol. 1, p. 729; B. E. Maryanoff and A. B. Reitz, Chem. Rev., 89, 863 (1989); L. Fitjer and U. Quabeck, Synth. Commun., 15, 855 (1985); A. R. Katritzky and J. Li, J. Org. Chem., 62, 238 (1997).
3. B. M. Trost, "Comprehensive Organic Synthesis," ed by S. E. Kelly, Pergamon Press, New York (1991), Vol. 1, p. 729; B. E. Maryanoff and A. B. Reitz, Chem. Rev., 89, 863 (1989); L. Fitjer and U. Quabeck, Synth. Commun., 15, 855 (1985); A. R. Katritzky and J. Li, J. Org. Chem., 62, 238 (1997).
4. B. M. Trost, "Comprehensive Organic Synthesis," ed by S. E. Kelly, Pergamon Press, New York (1991), Vol. 1, p. 729; B. E. Maryanoff and A. B. Reitz, Chem. Rev., 89, 863 (1989); L. Fitjer and U. Quabeck, Synth. Commun., 15, 855 (1985); A. R. Katritzky and J. Li, J. Org. Chem., 62, 238 (1997).
5. E. Erdik, "Organo Zinc Reagents in Organic Synthesis," CRC Press, Boca Raton, New York, London, and Tokyo (1993); R. L. Shriner, Org. React., 1, 1 (1942); M. W. Rathke, Org. React., 22, 423 (1975).
6. E. Erdik, "Organo Zinc Reagents in Organic Synthesis," CRC Press, Boca Raton, New York, London, and Tokyo (1993); R. L. Shriner, Org. React., 1, 1 (1942); M. W. Rathke, Org. React., 22, 423 (1975).
7. E. Erdik, "Organo Zinc Reagents in Organic Synthesis," CRC Press, Boca Raton, New York, London, and Tokyo (1993); R. L. Shriner, Org. React., 1, 1 (1942); M. W. Rathke, Org. React., 22, 423 (1975).
8. L. Lombardo, Org. Synth., 65, 81 (1987), and reference cited in; Y. Shen, Y. Xin, and J. Zhao, Tetrahedron Lett., 29, 6119 (1988) ; K. Takai, T. Kakiuchi, Y. Kataoka, and K. Utimoto, J. Org. Chem., 59, 2668 (1994); B. Castro, J. Villieras, and N. Ferracutti, Bull. Soc. Chim. Fr., 1969, 3521; K. Takai, Y. Hotta, K. Oshima, and H. Nozaki, Bull. Chem. Soc. Jpn., 53, 1698 (1980).
9. L. Lombardo, Org. Synth., 65, 81 (1987), and reference cited in; Y. Shen, Y. Xin, and J. Zhao, Tetrahedron Lett., 29, 6119 (1988) ; K. Takai, T. Kakiuchi, Y. Kataoka, and K. Utimoto, J. Org. Chem., 59, 2668 (1994); B. Castro, J. Villieras, and N. Ferracutti, Bull. Soc. Chim. Fr., 1969, 3521; K. Takai, Y. Hotta, K. Oshima, and H. Nozaki, Bull. Chem. Soc. Jpn., 53, 1698 (1980).
10. L. Lombardo, Org. Synth., 65, 81 (1987), and reference cited in; Y. Shen, Y. Xin, and J. Zhao, Tetrahedron Lett., 29, 6119 (1988) ; K. Takai, T. Kakiuchi, Y. Kataoka, and K. Utimoto, J. Org. Chem., 59, 2668 (1994); B. Castro, J. Villieras, and N. Ferracutti, Bull. Soc. Chim. Fr., 1969, 3521; K. Takai, Y. Hotta, K. Oshima, and H. Nozaki, Bull. Chem. Soc. Jpn., 53, 1698 (1980).
11. L. Lombardo, Org. Synth., 65, 81 (1987), and reference cited in; Y. Shen, Y. Xin, and J. Zhao, Tetrahedron Lett., 29, 6119 (1988) ; K. Takai, T. Kakiuchi, Y. Kataoka, and K. Utimoto, J. Org. Chem., 59, 2668 (1994); B. Castro, J. Villieras, and N. Ferracutti, Bull. Soc. Chim. Fr., 1969, 3521; K. Takai, Y. Hotta, K. Oshima, and H. Nozaki, Bull. Chem. Soc. Jpn., 53, 1698 (1980).
12. L. Lombardo, Org. Synth., 65, 81 (1987), and reference cited in; Y. Shen, Y. Xin, and J. Zhao, Tetrahedron Lett., 29, 6119 (1988) ; K. Takai, T. Kakiuchi, Y. Kataoka, and K. Utimoto, J. Org. Chem., 59, 2668 (1994); B. Castro, J. Villieras, and N. Ferracutti, Bull. Soc. Chim. Fr., 1969, 3521; K. Takai, Y. Hotta, K. Oshima, and H. Nozaki, Bull. Chem. Soc. Jpn., 53, 1698 (1980).
13. P. Knochel, "Active Metals," ed by A. Fürstner, VCH, Weinheim, New York, Basel, Cambridge, and Tokyo (1995), p. 191; A. Fürstner, Angew. Chem., Int. Ed. Engl., 32, 164 (1993); K. Takai, T. Kakiuchi, and K. Utimoto, J. Org. Chem., 59, 2671 (1994); H. Stadtmüller, B. Greve, K. Lennick, A. Chair, and P. Knochel, Synthesis, 1995, 69; G. Picotin and P. Miginiac, J. Org. Chem., 52, 4796 (1987).
14. P. Knochel, "Active Metals," ed by A. Fürstner, VCH, Weinheim, New York, Basel, Cambridge, and Tokyo (1995), p. 191; A. Fürstner, Angew. Chem., Int. Ed. Engl., 32, 164 (1993); K. Takai, T. Kakiuchi, and K. Utimoto, J. Org. Chem., 59, 2671 (1994); H. Stadtmüller, B. Greve, K. Lennick, A. Chair, and P. Knochel, Synthesis, 1995, 69; G. Picotin and P. Miginiac, J. Org. Chem., 52, 4796 (1987).
15. P. Knochel, "Active Metals," ed by A. Fürstner, VCH, Weinheim, New York, Basel, Cambridge, and Tokyo (1995), p. 191; A. Fürstner, Angew. Chem., Int. Ed. Engl., 32, 164 (1993); K. Takai, T. Kakiuchi, and K. Utimoto, J. Org. Chem., 59, 2671 (1994); H. Stadtmüller, B. Greve, K. Lennick, A. Chair, and P. Knochel, Synthesis, 1995, 69; G. Picotin and P. Miginiac, J. Org. Chem., 52, 4796 (1987).
16. P. Knochel, "Active Metals," ed by A. Fürstner, VCH, Weinheim, New York, Basel, Cambridge, and Tokyo (1995), p. 191; A. Fürstner, Angew. Chem., Int. Ed. Engl., 32, 164 (1993); K. Takai, T. Kakiuchi, and K. Utimoto, J. Org. Chem., 59, 2671 (1994); H. Stadtmüller, B. Greve, K. Lennick, A. Chair, and P. Knochel, Synthesis, 1995, 69; G. Picotin and P. Miginiac, J. Org. Chem., 52, 4796 (1987).
17. P. Knochel, "Active Metals," ed by A. Fürstner, VCH, Weinheim, New York, Basel, Cambridge, and Tokyo (1995), p. 191; A. Fürstner, Angew. Chem., Int. Ed. Engl., 32, 164 (1993); K. Takai, T. Kakiuchi, and K. Utimoto, J. Org. Chem., 59, 2671 (1994); H. Stadtmüller, B. Greve, K. Lennick, A. Chair, and P. Knochel, Synthesis, 1995, 69; G. Picotin and P. Miginiac, J. Org. Chem., 52, 4796 (1987).
18. Pd/Ti and Zn/Cu couples promoted reductive homo-coupling reactions of benzylidene dichlorides or dichloroacetates were reported. see: S. Mataka, G-B. L. Liu, and M. Tashiro, Synthesis, 1995, 133; T. Nakano, M. Takahashi, T. Ashizawa, T. Arai, S. Seki, H. Matsumoto, and Y. Nagai, Chem. Lett., 1982, 613; T. Allmendinger and R. W. Lang, Tetrahedron Lett., 32, 339 (1991).
19. Pd/Ti and Zn/Cu couples promoted reductive homo-coupling reactions of benzylidene dichlorides or dichloroacetates were reported. see: S. Mataka, G-B. L. Liu, and M. Tashiro, Synthesis, 1995, 133; T. Nakano, M. Takahashi, T. Ashizawa, T. Arai, S. Seki, H. Matsumoto, and Y. Nagai, Chem. Lett., 1982, 613; T. Allmendinger and R. W. Lang, Tetrahedron Lett., 32, 339 (1991).
20. Pd/Ti and Zn/Cu couples promoted reductive homo-coupling reactions of benzylidene dichlorides or dichloroacetates were reported. see: S. Mataka, G-B. L. Liu, and M. Tashiro, Synthesis, 1995, 133; T. Nakano, M. Takahashi, T. Ashizawa, T. Arai, S. Seki, H. Matsumoto, and Y. Nagai, Chem. Lett., 1982, 613; T. Allmendinger and R. W. Lang, Tetrahedron Lett., 32, 339 (1991).
21. 2 instead of 85% Zn brought about the formation of 3a in the yield of 68 and 46%, respectively.
22. In this reaction, roles of TMSCl may be postulated mainly two ways, that is, one is activation of zinc metal surface and another one is activation of 2 by coordination to carbonyl group.
23. 1HNMR and/or gas chromatography according to the reported assignment. For example: O. H. Wheeler and H. N. Barle de Pabon, J. Org. Chem., 30, 1473 (1965); Y. Fujiwara, I. Moritani, S. Danno, R. Asano, and S. Teranishi, J. Am. Chem. Soc., 91, 7166 (1969); F. Akiyama, H. Miyazaki, K. Kaneda, S. Teranishi, Y. Fujiwara, M. Abe, and H. Taniguchi, J. Org. Chem., 45, 2359 (1980).
24. 1HNMR and/or gas chromatography according to the reported assignment. For example: O. H. Wheeler and H. N. Barle de Pabon, J. Org. Chem., 30, 1473 (1965); Y. Fujiwara, I. Moritani, S. Danno, R. Asano, and S. Teranishi, J. Am. Chem. Soc., 91, 7166 (1969); F. Akiyama, H. Miyazaki, K. Kaneda, S. Teranishi, Y. Fujiwara, M. Abe, and H. Taniguchi, J. Org. Chem., 45, 2359 (1980).
25. 1HNMR and/or gas chromatography according to the reported assignment. For example: O. H. Wheeler and H. N. Barle de Pabon, J. Org. Chem., 30, 1473 (1965); Y. Fujiwara, I. Moritani, S. Danno, R. Asano, and S. Teranishi, J. Am. Chem. Soc., 91, 7166 (1969); F. Akiyama, H. Miyazaki, K. Kaneda, S. Teranishi, Y. Fujiwara, M. Abe, and H. Taniguchi, J. Org. Chem., 45, 2359 (1980).