Aminomethylation of enals through carbene and acid cooperative catalysis: concise access to β(2)-amino acids

Angewandte Chemie
Jianfeng XuYonggui Robin Chi

Abstract

A convergent, organocatalytic asymmetric aminomethylation of α,β-unsaturated aldehydes by N-heterocyclic carbene (NHC) and (in situ generated) Brønsted acid cooperative catalysis is disclosed. The catalytically generated conjugated acid from the base plays dual roles in promoting the formation of azolium enolate intermediate, formaldehyde-derived iminium ion (as an electrophilic reactant), and methanol (as a nucleophilic reactant). This redox-neutral strategy is suitable for the scalable synthesis of enantiomerically enriched β(2) -amino acids bearing various substituents.

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Citations

Jul 1, 2015·Organic & Biomolecular Chemistry·Suleman M InamdarNitin T Patil
Jan 23, 2018·Chemical Communications : Chem Comm·Linrui ZhangYong Huang
Feb 16, 2020·Angewandte Chemie·Min ZhouRunhui Liu
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Aug 29, 2019·Frontiers in Chemistry·Carmine OstacoloAlessia Bertamino
Aug 24, 2017·Chemistry : a European Journal·Shunxi DongCarsten Bolm
Jun 23, 2016·Angewandte Chemie·Wenlong WangFuwei Li
Mar 2, 2021·Journal of the American Chemical Society·Chendan ZhuBenjamin List
Mar 3, 2021·Chemical Communications : Chem Comm·Xianfan QiuChuanzhou Tao
Mar 25, 2021·Journal of the American Chemical Society·Kun Liu, Armido Studer
Jun 23, 2021·Organic & Biomolecular Chemistry·Zhiqiong TangLu Liu
Dec 10, 2016·Journal of the American Chemical Society·Qi SunShengqian Ma
Mar 1, 2019·Organic Letters·Jianliang YuJiangtao Sun

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