Organic letters

Kinetic Resolution of Racemic 1-Alkyl-2-methylenecyclopropanes via Palladium-Catalyzed Silaborative C− C Cleavage

T Ohmura, H Taniguchi, M Suginome

Index: Ohmura, Toshimichi; Taniguchi, Hiroki; Suginome, Michinori Organic Letters, 2009 , vol. 11, # 13 p. 2880 - 2883

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Citation Number: 27

Abstract

Kinetic resolution of racemic 1-alkyl-2-methylenecyclopropanes via silaborative C− C cleavage was efficiently catalyzed by a palladium complex bearing a chiral phosphoramidite, affording 2-boryl-3-silylmethyl-1-alkenes as major products with up to 92% ee. Enantioenrichment through parallel kinetic resolution, where the slower reacting enantiomer was converted to the constitutional isomer of the major product, may be ...