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
收藏
页码：4599 / 4603
页数：5
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