Ni-Catalyzed Formation of Two Vicinal Enantioenriched C(sp³) Centers Stemming from Two Starting Materials

Key words

nickel catalysis - hydroalkylation - enantioselectivity - diastereoselectivity - radicals

Significance

The Hu group reports the first enantio- and diastereoselective Ni-catalyzed hydroalkylation of prochiral alkenes with a racemic mixture of a chiral alkyl halide. This report is the first example where control of a C(sp³)–C(sp³) bond formation occurs stereoselectively, as previous methodologies only lead to poor or modest diastereoselectivities.

Comment

The reaction generates products containing enantioenriched alkyl boronate and alkyl lactam moieties, which are both useful intermediates in organic synthesis. A ‘time study’ revealed that the racemic alkyl halides react through an enantioconvergent process instead of a kinetic resolution.