Asymmetric conjugate additions of alkylzirconocenes to cyclopent-4-ene-1,3-dione monoacetals.

Copper-catalyzed asymmetric conjugate additions are powerful reactions that allow the formation of single-enantiomer building blocks in a few steps. However, highly enantioselective conjugate addition to five-membered-ring substrates is more challenging and is often neglected. Here, we report cataly...

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Bibliographic Details
Main Authors: Rideau, E, Masing, F, Fletcher, S
Format: Journal article
Language:English
Published: 2015
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Summary:Copper-catalyzed asymmetric conjugate additions are powerful reactions that allow the formation of single-enantiomer building blocks in a few steps. However, highly enantioselective conjugate addition to five-membered-ring substrates is more challenging and is often neglected. Here, we report catalytic asymmetric 1,4-addition of alkylzirconocenes, formed in situ from readily available alkenes, to cyclopent-4-ene-1,3-dione monoacetals. Good to high enantioselectivities are observed and the procedure tolerates various functional groups.