Cu-Catalyzed Enantioselective Reductive Coupling of 1,3-Dienes and Carboxylic Acid Anhydrides

Catalytic chemo-, regio- and enantioselective construction of allyl-Cu complexes generated from a Cu-H addition to trans-1,3-dienes followed by in situ addition to anhydrides to construct homoallylic alcohols is presented. This method is distinguished by a characteristic pathway to generate enantiomerically enriched allyl-Cu species, which react with a wide range of anhydrides in high chemo-, regio- and stereoselectivity. Functionalization of homoallylic alcohol products provides useful building blocks which are otherwise difficult to obtain. The Cu-H catalyzed enantioselective reductive coupling of 1,3-dienes and anhydrides via enantioenriched allyl-Cu species is reported herein, affording homoallylic alcohols bearing Z-alkenes in good yield and enantioselectivity. Functionalization of the homoallylic alcohol shows a unique approach to synthesis of cis-1,3-diol in high yield and diastereoselectivity.image

Automated summary

A catalytic method for the construction of homoallylic alcohols from trans-1,3-dienes and anhydrides is presented. This method involves the generation of enantiomerically enriched allyl-Cu species which react selectively with a wide range of anhydrides. The functionalization of homoallylic alcohol products provides useful building blocks that are difficult to obtain through other methods.