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Enantioselective Addition of α-Nitroesters to Alkynes.

Authors :
Davison RT
Parker PD
Hou X
Chung CP
Augustine SA
Dong VM
Source :
Angewandte Chemie (International ed. in English) [Angew Chem Int Ed Engl] 2021 Feb 23; Vol. 60 (9), pp. 4599-4603. Date of Electronic Publication: 2021 Jan 07.
Publication Year :
2021

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 <superscript>III</superscript> -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.<br /> (© 2021 Wiley-VCH GmbH.)

Details

Language :
English
ISSN :
1521-3773
Volume :
60
Issue :
9
Database :
MEDLINE
Journal :
Angewandte Chemie (International ed. in English)
Publication Type :
Academic Journal
Accession number :
33411337
Full Text :
https://doi.org/10.1002/anie.202014015