Synthesis

Palladium-catalyzed silastannation of secondary propargylic alcohols and their derivatives

TE Nielsen, S Le Quement, D Tanner

Index: Nielsen, Thomas E.; Le Quement, Sebastian Le; Tanner, David Synthesis, 2004 , # 9 p. 1381 - 1390

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Citation Number: 20

Abstract

Abstract A series of terminal propargylic alcohols and their derivatives were subjected to Pd- catalyzed silastannation. In all reactions, complete regio-and stereoselectivities were observed with the tributyltin moiety exclusively adding to the internal carbon of the triple bond in a cis fashion, including the first example of a diyne bis-silastannation. Silastannation reaction products could sequentially be protiodesilylated or iododestannylated, thus ...