Access to β2-Amino Acids via Enantioselective 1,4-Arylation of β-Nitroacrylates Catalyzed by Chiral Rhodium Catalysts

J Org Chem. 2018 Oct 5;83(19):12184-12191. doi: 10.1021/acs.joc.8b00586. Epub 2018 Sep 12.

Abstract

The highly enantioselective conjugate addition of a variety of arylboronic acids to β-nitroacrylates is reported to provide optically active α-aryl β-nitropropionates in up to 70% yields and >99.5% ee's, which are useful building blocks for preparing chiral β2-amino acids. The applicability of this transformation is demonstrated by converting 3aa into the β2-amino acid 5 and transforming 3ap to β-amino ester 7 via reduction and reductive N-alkylation. The latter compound is a precursor for preparing ent-ipatasertib.

Publication types

  • Research Support, Non-U.S. Gov't