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

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 is tolerant of a variety of cross partners, varying in functionality and steric profile.

SUBMITTER: Quigley BL

PROVIDER: S-EPMC4339074 | biostudies-literature | 2014 Feb

REPOSITORIES: biostudies-literature

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

Quigley Brendan L BL Grubbs Robert H RH

Chemical science 20140201 2

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 is tolerant of a variety o ...[more]

PMID: 25722847

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