A catalytic system consisting of vanadium, chlorosilane, and aluminum metal in the stereoselective pinacol coupling reaction of benzaldehyde derivatives

Journal of Organic Chemistry

Volumn 64, Issue 20, 1999, Pages 7665-7667

  Hirao, Toshikazu ^a   Hatano, Bunpei ^a   Imamoto, Yuka ^a   Ogawa, Akiya ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALUMINUM; BENZALDEHYDE DERIVATIVE; CHLOROSILANE; SILANE DERIVATIVE; UNCLASSIFIED DRUG; VANADIUM;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL STRUCTURE; ELECTRON TRANSPORT; REACTION ANALYSIS; REDUCTION;

EID: 0033214637     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo990902m     Document Type: Article

References (27)

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21. 3 and Zn powder was effective for the stoichiometric reductive coupling of aldehydes: (a) Kang, M.; Park, J.; Pedersen, S. F. Synlett 1997, 41. (b) Konradi, A.; Kemp, S.; Pedersen, S. F. J. Am. Chem. Soc. 1994, 116, 1316. (c) Konradi, A. W.; Pedersen, S. F. J. Org. Chem. 1992, 57, 28. (d) Raw, A. S.; Pedersen, S. F. J. Org. Chem. 1991, 56, 830. (e) Freudenberger, J. H.; Konradi, A. W.; Pedersen, S. F. J. Am. Chem. Soc. 1989, 111, 8014. (f) Annunziata, R.; Benaglia, M.; Cinquini, M.; Cozzi, F.; Giaroni, P. J. Org. Chem. 1991, 57, 782. (g) Kammermeier, B.; Beck, G.; Jacobi, D.; Jendralla, H. Angew. Chem., Int. Ed. Engl. 1994, 33, 685.
22. 3 and Zn powder was effective for the stoichiometric reductive coupling of aldehydes: (a) Kang, M.; Park, J.; Pedersen, S. F. Synlett 1997, 41. (b) Konradi, A.; Kemp, S.; Pedersen, S. F. J. Am. Chem. Soc. 1994, 116, 1316. (c) Konradi, A. W.; Pedersen, S. F. J. Org. Chem. 1992, 57, 28. (d) Raw, A. S.; Pedersen, S. F. J. Org. Chem. 1991, 56, 830. (e) Freudenberger, J. H.; Konradi, A. W.; Pedersen, S. F. J. Am. Chem. Soc. 1989, 111, 8014. (f) Annunziata, R.; Benaglia, M.; Cinquini, M.; Cozzi, F.; Giaroni, P. J. Org. Chem. 1991, 57, 782. (g) Kammermeier, B.; Beck, G.; Jacobi, D.; Jendralla, H. Angew. Chem., Int. Ed. Engl. 1994, 33, 685.
23. 3 and Zn powder was effective for the stoichiometric reductive coupling of aldehydes: (a) Kang, M.; Park, J.; Pedersen, S. F. Synlett 1997, 41. (b) Konradi, A.; Kemp, S.; Pedersen, S. F. J. Am. Chem. Soc. 1994, 116, 1316. (c) Konradi, A. W.; Pedersen, S. F. J. Org. Chem. 1992, 57, 28. (d) Raw, A. S.; Pedersen, S. F. J. Org. Chem. 1991, 56, 830. (e) Freudenberger, J. H.; Konradi, A. W.; Pedersen, S. F. J. Am. Chem. Soc. 1989, 111, 8014. (f) Annunziata, R.; Benaglia, M.; Cinquini, M.; Cozzi, F.; Giaroni, P. J. Org. Chem. 1991, 57, 782. (g) Kammermeier, B.; Beck, G.; Jacobi, D.; Jendralla, H. Angew. Chem., Int. Ed. Engl. 1994, 33, 685.
24. 3 and Zn powder was effective for the stoichiometric reductive coupling of aldehydes: (a) Kang, M.; Park, J.; Pedersen, S. F. Synlett 1997, 41. (b) Konradi, A.; Kemp, S.; Pedersen, S. F. J. Am. Chem. Soc. 1994, 116, 1316. (c) Konradi, A. W.; Pedersen, S. F. J. Org. Chem. 1992, 57, 28. (d) Raw, A. S.; Pedersen, S. F. J. Org. Chem. 1991, 56, 830. (e) Freudenberger, J. H.; Konradi, A. W.; Pedersen, S. F. J. Am. Chem. Soc. 1989, 111, 8014. (f) Annunziata, R.; Benaglia, M.; Cinquini, M.; Cozzi, F.; Giaroni, P. J. Org. Chem. 1991, 57, 782. (g) Kammermeier, B.; Beck, G.; Jacobi, D.; Jendralla, H. Angew. Chem., Int. Ed. Engl. 1994, 33, 685.
25. 3 and Zn powder was effective for the stoichiometric reductive coupling of aldehydes: (a) Kang, M.; Park, J.; Pedersen, S. F. Synlett 1997, 41. (b) Konradi, A.; Kemp, S.; Pedersen, S. F. J. Am. Chem. Soc. 1994, 116, 1316. (c) Konradi, A. W.; Pedersen, S. F. J. Org. Chem. 1992, 57, 28. (d) Raw, A. S.; Pedersen, S. F. J. Org. Chem. 1991, 56, 830. (e) Freudenberger, J. H.; Konradi, A. W.; Pedersen, S. F. J. Am. Chem. Soc. 1989, 111, 8014. (f) Annunziata, R.; Benaglia, M.; Cinquini, M.; Cozzi, F.; Giaroni, P. J. Org. Chem. 1991, 57, 782. (g) Kammermeier, B.; Beck, G.; Jacobi, D.; Jendralla, H. Angew. Chem., Int. Ed. Engl. 1994, 33, 685.
26. Stang, J. P.; Hanack, M.; Subramanian, R. L. Synthesis 1982, 85.
27. The stereoselectivity for the formation of diols and diaminee is described in ref 5d; a cyclic intermediate is suggested to favor the formation of the dl-isomer. On the other hand, an acyclic intermediate is proposed to give meso-selectivity. Although the role of a co-reductant requires further detailed mechanistic experiment, it may affect the transition state. equation presented