Access to Stereodefined Multifunctionalized β,γ-Unsaturated Ketones via Chemo-, Regio- and Diastereoselective Copper-Catalyzed Diborylation of Cross-Conjugated Enynones†

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.

Automated summary

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.