Aminomethylation of enals through carbene and acid cooperative catalysis : concise access to β2-amino acids

Aminomethylation of enals through carbene and acid cooperative catalysis : concise access to β2-amino acids

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 az...

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Bibliographic Details
Main Authors: Chi, Robin Yonggui, Xu, Jianfeng, Chen, Xingkuan, Wang, Ming, Zheng, Pengcheng, Song, Bao-An
Other Authors: School of Physical and Mathematical Sciences
Format: Article
Language:English
Published: 2015
Subjects:
DRNTU::Science::Chemistry::Physical chemistry::Catalysis
Online Access:https://hdl.handle.net/10356/107124
http://hdl.handle.net/10220/25281
http://dx.doi.org/10.1002/anie.201412132
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Institution: Nanyang Technological University
Language: English
Description
Summary: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 β2-amino acids bearing various substituents.

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