REGIO- AND STREREO-SELECTIVE SYNTHESIS OF VINYLSTANNANES. TRANSITION-METAL CATALYZED STANNYLMETALATION OF ACETYLENES AND CONVERSION OF ENOL TRIFLATES AND VINYL IODIDES INTO VINYLSTANNANES

Article abstract of DOI:10.1016/0022-328X(85)87365-4

Two new methods for the regio- and strereo-selective synthesis of vinylstannanes are described. (i) The reaction of terminal acetylenes with n-Bu3SnMgMe, n-Bu3SnAlEt2, or (n-Bu3Sn)2Zn in the presence of various transition-metal catalysts provides vinylstannanes in good yields.Whereas copper-catalyzed stannylmagnesation of 4-benzyloxy-1-butyne gives (E)-4-benzyloxy-1-tributylstannyl-1-butene exclusively, palladium-catalyzed stannylzincation affords 4-benzyloxy-2-tributylstannyl-1-butene preferentially. (ii) Treatment of enol triflates or vinyl iodide with Me3Sn-MgMe in the presence of CuCN catalyst gives vinylstannanes in good yields.