Access to cyclic β-amino acids by amine-catalyzed enantioselective addition of the γ-carbon atoms of α,β-unsaturated imines to enals

Access to cyclic β-amino acids by amine-catalyzed enantioselective addition of the γ-carbon atoms of α,β-unsaturated imines to enals

Disclosed herein is a new catalytic approach for an efficient access to cyclic β-amino acids widely found in bioactive small molecules and peptidic foldamers. Our method involves addition of the remote γ-carbon atoms of α,β-unsaturated imines to enals by iminium organic catalysis. This highly chemo-...

Full description

Saved in:
Bibliographic Details
Main Authors: Luo, Guoyong, Huang, Zhijian, Zhuo, Shitian, Mou, Chengli, Wu, Jian, Jin, Zhichao, Chi, Robin Yonggui
Other Authors: School of Physical and Mathematical Sciences
Format: Article
Language:English
Published: 2020
Subjects:
Science::Chemistry::Organic chemistry
Amine Catalysis
Cyclic β-Amino Acid
Online Access:https://hdl.handle.net/10356/137752
Tags: Add Tag
No Tags, Be the first to tag this record!
Institution: Nanyang Technological University
Language: English
Description
Summary:Disclosed herein is a new catalytic approach for an efficient access to cyclic β-amino acids widely found in bioactive small molecules and peptidic foldamers. Our method involves addition of the remote γ-carbon atoms of α,β-unsaturated imines to enals by iminium organic catalysis. This highly chemo- and stereo-selective reaction affords cyclic β-amino aldehydes that can be converted to amino acids bearing quaternary stereocenters with exceptional optical purities. Our study demonstrates the unique power of organic catalytic remote carbon reactions in rapid synthesis of functional molecules.

Similar Items