Diastereoselective Allylation of Aldehydes by Dual Photoredox and Chromium Catalysis

J Am Chem Soc. 2018 Oct 10;140(40):12705-12709. doi: 10.1021/jacs.8b08052. Epub 2018 Sep 26.

Abstract

Herein, we report the redox-neutral allylation of aldehydes with readily available electron-rich allyl (hetero-) arenes, β-alkyl styrenes and allyl-diarylamines. This process was enabled by the combination of photoredox and chromium catalysis, which allowed a range of homoallylic alcohols to be prepared with high levels of selectivity for the anti diastereomer. Mechanistic investigations support the formation of an allyl chromium intermediate from allylic C(sp3)-H bonds and thus significantly extends the scope of the venerable Nozaki-Hiyama-Kishi reaction.

Publication types

  • Research Support, Non-U.S. Gov't