Organic letters

trans-Hydrometalation of alkynes by a combination of InCl3 and DIBAL-H: One-pot access to functionalized (Z)-alkenes

K Takami, H Yorimitsu, K Oshima

Index: Takami, Kazuaki; Yorimitsu, Hideki; Oshima, Koichiro Organic Letters, 2002 , vol. 4, # 17 p. 2993 - 2995

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Citation Number: 83

Abstract

Triethylborane-induced hydrometalation of alkynes proceeds in an anti manner to afford the corresponding (Z)-alkenylmetal compounds stereoselectively, where dichloroindium hydride would play a key role. A variety of functional groups including hydroxy, carbonyl, and carboxy groups were tolerant under the reaction conditions. Following iodolysis and cross- coupling reaction of the (Z)-alkenylmetal species show the usefulness of this strategy.