Journal
CHINESE JOURNAL OF CHEMISTRY
Volume 39, Issue 3, Pages 590-596Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/cjoc.202000475
Keywords
Stereoselectivity; β γ ‐ Unsaturated ketones; Copper catalysis; Borylation; Cross‐ conjugated enynones
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The study presented a mild, rapid copper-catalyzed diborylation reaction for the synthesis of stereodefined multifunctionalized beta,gamma-unsaturated ketones. Fine control of chemo-, regio-, Z/E and diastereoselectivity was achieved, expanding the substrate scope and proposing a possible catalytic cycle to explain the selectivity.
Main observation and conclusion Stereodefined beta,gamma-unsaturated carbonyl compounds are important yet synthetically challenging units in natural products and drugs. Disclosed herein is a mild, rapid copper-catalyzed diborylation reaction of cross-conjugated enynones as a step-economic and modular approach to stereodefined multifunctionalized beta,gamma-unsaturated ketones by fine control of chemo-, regio-, Z/E and diastereoselectivity. The substrate scope was examined and a possible catalytic cycle was proposed to explain the multifaceted selectivity.
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