학술논문

Enantioselective Addition of α‐Nitroesters to Alkynes
Document Type
article
Source
Angewandte Chemie International Edition. 60(9)
Subject
Inorganic Chemistry
Organic Chemistry
Chemical Sciences
Alkynes
Amino Acids
Catalysis
Coordination Complexes
Esters
Hydrogen
Rhodium
Stereoisomerism
alkynes
amino acids
nitroester
rhodium hydride
tandem catalysis
Chemical sciences
Language
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 RhIII -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.