Enantioselective Addition of α-Nitroesters to Alkynes

被引：27

作者：

Davison, Ryan T. ^{[1
]}

Parker, Patrick D. ^{[1
]}

Hou, Xintong ^{[1
]}

Chung, Crystal P. ^{[1
]}

Augustine, Sara A. ^{[1
]}

Dong, Vy M. ^{[1
]}

机构：

[1] Univ Calif Irvine, Dept Chem, Irvine, CA 92697 USA

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2021年 / 60卷 / 09期

基金：

美国国家卫生研究院;

关键词：

alkynes; amino acids; nitroester; rhodium hydride; tandem catalysis; NONNATURAL AMINO-ACIDS; CATALYTIC ASYMMETRIC-SYNTHESIS; ALLYLIC ALKYLATION; PRIMARY ALCOHOLS; STEREOSELECTIVE-SYNTHESIS; 1,3-DICARBONYL COMPOUNDS; VICINAL TERTIARY; TERMINAL ALKYNES; ALLYLATION; QUATERNARY;

D O I：

10.1002/anie.202014015

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

By using Rh-H catalysis, we couple alpha-nitroesters and alkynes to prepare alpha-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-pi-allyl electrophile, which is trapped by an alpha-nitroester nucleophile. A subsequent reduction with In powder transforms the allylic alpha-nitroesters to the corresponding alpha,alpha-disubstituted alpha-amino esters.

引用

页码：4599 / 4603

页数：5

共 88 条

[1]

[Anonymous], ANGEW CHEM

[2] Regioselective Rhodium-Catalyzed Addition of -Keto Esters, -Keto Amides, and 1,3-Diketones to Internal Alkynes [J].