Regioselective addition of trimethylstannylcopper-dimethyl sulphide to 1-alkynes: Synthesis of ω-substituted 2-(trimethylstannyl)-1-alkenes

Journal of the Chemical Society, Chemical Communications

Volumn , Issue 17, 1983, Pages 934-935

  Piers, Edward ^a   Chong, J Michael ^a  

^a UNIVERSITY OF BRITISH COLUMBIA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 37049097718     PISSN: 00224936     EISSN: None     Source Type: Journal    
DOI: 10.1039/C39830000934     Document Type: Article

References (8)

1. E. Piers and V. Karunaratne, J. Org. Chem., 1983, 48, 1774.
2. D. Seebach, Angew. Chem., Int. Ed. Engl., 1979, 18, 239.
3. E. Piers, J. M. Chong, and H. E. Morton, Tetrahedron Lett., 1981, 22, 4905.
4. Although a recent report (H. Westmijze, K. Ruitenberg, J. Meijer, and P. Vermeer, Tetrahedron Lett., 1982, 23, 2797) described the addition of triphenylstannylcopper to acetylene itself, the addition of trialkylstannylcopper reagents to terminal alkynes has not been reported previously.
5. S. D. Cox and F. Wudl, Organometallics, 1983, 2, 184.
6. E. Piers and H. E. Morton, J. Org. Chem., 1980, 45, 4263.
7. It should be noted that hydrostannation of terminal alkynes with trialkylstannanes usually provides only minor amounts of 2-trialkylstannyl-l-alkenes: E. Negishi, ‘Organometallics in Organic Synthesis,’ Wiley, New York, 1980, p. 411.
8. M. E. Jung and L. A. Light, Tetrahedron Lett., 1982, 23, 3851, and references cited therein.