Chemical Science

Ruthenium-catalysed Z-selective cross metathesis of allylic-substituted olefins

BL Quigley, RH Grubbs

Index: Quigley, Brendan L.; Grubbs, Robert H. Chemical Science, 2014 , vol. 5, # 2 p. 501 - 506

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Citation Number: 37

Abstract

The Z-selective cross metathesis of allylic-substituted olefins is explored with recently developed ruthenium-based metathesis catalysts. The reaction proceeds with excellent stereoselectivity for the Z-isomer (typically> 95%) and yields of up to 88% for a variety of allylic substituents. This includes the first synthesis of Z-α, β-unsaturated acetals by cross metathesis and their elaboration to Z-α, β-unsaturated aldehydes. In addition, the reaction ...