Palladium-Catalyzed Chiral Transfer Three-Component Reaction for the Synthesis of 1,2,4-Trisubstituted Homoallylic Alcohols

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Abstract

1,2,4-Trisubstituted chiral homoallylic alcohols are valuable intermediates in natural product synthesis and complex molecular architectures; however, their asymmetric catalytic synthesis remains challenging due to the need for simultaneous and precise control of regioselectivity, diastereoselectivity, E/Z geometry, and enantioselectivity. Herein, we report a chiral transfer reaction based on a palladium-catalyzed three-component reaction of aldehydes, borylated allyl acetate, dimethylzinc for the efficient synthesis of 1,2,4-trisubstituted anti-(Z)-chiral homoallylic alcohol derivatives. Readily accessible borylated chiral homoallylic alcohols, prepared for example via Sharpless asymmetric epoxidation, serve as effective starting materials, allowing highly stereocontrolled formation of 1,2,4-trisubstituted anti-(Z)-chiral homoallylic alcohols.

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