Regio- and stereo-selective synthesis of vinylstannanes. Transition-metal catalyzed stannylmetalation of acetylenes and conversion of enol triflates and vinyl iodides into vinylstannanes
作者:Seijiro Matsubara、Jun-Ichi Hibino、Yoshitomi Morizawa、Koichiro Oshima、Hitosi Nozaki
DOI:10.1016/0022-328x(85)87365-4
日期:1985.4
Two new methods for the regio- and stereo-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
描述了乙烯基锡烷的区域和立体选择性合成的两种新方法。(i)在各种过渡金属催化剂存在下,末端乙炔与n-Bu 3 SnMgMe,n-Bu 3 SnAlEt 2或(n-Bu 3 Sn)2 Zn的反应提供了高产率的乙烯基锡烷。铜催化的4-苄氧基-1-丁炔的苯乙烯甲基化仅得到(E)-4-苄氧基-1-三丁基锡烷基-1-丁烯,而钯催化的苯乙烯化锌则优先提供4-苄氧基-2-三丁基锡烷基-1-丁烯。(ii)在CuCN催化剂存在下用Me 3 Sn-MgMe处理烯醇三氟甲磺酸酯或碘乙烯,得到高产率的乙烯基锡烷。