Journal
ORGANIC LETTERS
Volume 22, Issue 20, Pages 8096-8100Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.0c03046
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Funding
- China Scholarship Council
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A copper-catalyzed deconjugative addition of silicon nucleophiles to a broad range of enyne-type alpha,ss,gamma,delta-unsaturatedacceptors with high enantiocontrol is reported. The method is 1,4-selective with hardly any formation of the 1,6-adduct. The double-bond geometry is shown to be critical for achieving this chemoselectivity: exclusive 1,4-addition for E and predominant 1,6-addition for Z. By this, E-configured enynoates, enynamides, and enynones have been converted to the corresponding a-chiral propargylic silanes with excellent enantiomeric excesses.
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