Enantioselective Addition of α-Nitroesters to Alkynes.

ABSTRACT: By using Rh-H catalysis, we couple α-nitroesters and alkynes to prepare α-amino-acid precursors. This atom-economical strategy generates two contiguous stereocenters, with high enantio- and diastereocontrol. In this transformation, the alkyne undergoes isomerization to generate a Rh^III -π-allyl electrophile, which is trapped by an α-nitroester nucleophile. A subsequent reduction with In powder transforms the allylic α-nitroesters to the corresponding α,α-disubstituted α-amino esters.

SUBMITTER: Davison RT 

PROVIDER: S-EPMC7927945 | biostudies-literature | 2021 Feb

REPOSITORIES: biostudies-literature