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

• المؤلفون الرئيسيون: Chi, Robin Yonggui, Xu, Jianfeng, Chen, Xingkuan, Wang, Ming, Zheng, Pengcheng, Song, Bao-An
• مؤلفون آخرون: School of Physical and Mathematical Sciences
• التنسيق: مقال
• اللغة: English
• منشور في: 2015
• الموضوعات: DRNTU::Science::Chemistry::Physical chemistry::Catalysis
• الوصول للمادة أونلاين: https://hdl.handle.net/10356/107124; http://hdl.handle.net/10220/25281; http://dx.doi.org/10.1002/anie.201412132
• المؤسسة: Nanyang Technological University

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.