Lewis acid-catalyzed hydrostannation of acetylenes. Regio- and stereoselective trans-addition of tributyltin hydride and dibutyltin dihydride

Journal of Organic Chemistry

Volumn 61, Issue 14, 1996, Pages 4568-4571

  Asao, Naoki ^a,b   Liu, Jian Xiu ^a   Sudoh, Tomoko ^a   Yamamoto, Yoshinori ^a  

^a TOHOKU UNIVERSITY   (Japan)

^b HOKKAIDO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000531264     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo952273w     Document Type: Article

References (26)

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6. (a) The use of AIBN as a radical initiator; ref 1.
7. 3B: Nozaki, K.; Oshima, K.; Utimoto, K. J. Am. Chem. Soc. 1987, 109, 2547. Nozaki, K.; Oshima, K.; Utimoto, K. Bull. Chem. Soc. Jpn. 1987, 60, 3465.
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12. (a) Pd catalysts; Ichinose, Y.; Oda, H.; Oshima, K.; Utimoto, K. Bull. Chem. Soc. Jpn. 1987, 60, 3468. Zhang, H. X.; Guibe, F.; Balavoine, G. Tetrahedron Lett. 1988, 29, 619. Miyake, H.; Yamamura, K. Chem.Lett. 1989, 981.
13. (a) Pd catalysts; Ichinose, Y.; Oda, H.; Oshima, K.; Utimoto, K. Bull. Chem. Soc. Jpn. 1987, 60, 3468. Zhang, H. X.; Guibe, F.; Balavoine, G. Tetrahedron Lett. 1988, 29, 619. Miyake, H.; Yamamura, K. Chem.Lett. 1989, 981.
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18. The sonochemical hydrostannation produces the anti-hydrostannation product stereoselectively (ref 2c).
19. The cyclic divinyltin derivatives were produced by the hydrostannation of diynes under heat conditions. Keusink, A. J.; Nottes, J. G.; Bussing, H. A.; van der Kerk, G. J. M. Recl. Trav. Chim. Pays-Bas 1964, 83, 1036. Ashe, A. J., III; Shu, P. J. Am. Chem. Soc. 1971, 93, 1804 and references cited therein.
20. The cyclic divinyltin derivatives were produced by the hydrostannation of diynes under heat conditions. Keusink, A. J.; Nottes, J. G.; Bussing, H. A.; van der Kerk, G. J. M. Recl. Trav. Chim. Pays-Bas 1964, 83, 1036. Ashe, A. J., III; Shu, P. J. Am. Chem. Soc. 1971, 93, 1804 and references cited therein.
21. Asao, N.; Liu, J.-X.; Sudoh, T.; Yamamoto, Y. J. Chem. Soc., Chem. Commun., 1995, 2405.
22. As a byproduct, 1-octene was produced.
23. 3 complex was suggested. Yamamoto, K.; Takemae, M. Synlett 1990, 259.
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