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Published October 30, 2013 | Supplemental Material + Published
Journal Article Open

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


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.

Additional Information

© 2014 The Royal Society of Chemistry. Received 9th October 2013; Accepted 29th October 2013; First published online 30 Oct 2013. This work was financially supported by the NIH (R01GM031332). NMR spectra were obtained on instruments funded by the NIH (RR027690). Materia Inc. is gratefully acknowledged for donation of metathesis catalysts 1–4. S. M. Bronner, J. S. Cannon, M. B. Herbert and V. M. Marx are thanked for helpful discussion.

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Supplemental Material - c3sc52806e_si.pdf


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