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Counterion-induced asymmetric control in ring-opening of azetidiniums: facile access to chiral amines

Citation

Qian, D and Chen, M and Bissember, AC and Sun, J, Counterion-induced asymmetric control in ring-opening of azetidiniums: facile access to chiral amines, Angewandte Chemie International Edition, 57, (14) pp. 3763-3766. ISSN 1433-7851 (2018) [Refereed Article]

Copyright Statement

Copyright 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

DOI: doi:10.1002/anie.201712395

Abstract

Counterion-induced stereocontrol is a powerful tool in organic synthesis. However, such enantiocontrol on tetrahedral ammonium cations remains challenging. Described here is the first example of using chiral anion phase-transfer catalysis to achieve intermolecular ring-opening of azetidiniums with excellent enantioselectivity (up to 97% ee). Precise control over the formation and reaction of the chiral ion pair as well as inhibition of the background reaction by the biphasic system is key to the success of the reaction.

Item Details

Item Type:Refereed Article
Keywords:organocatalysis, phase-transfer catalysis, azetidiniums
Research Division:Chemical Sciences
Research Group:Organic Chemistry
Research Field:Organic Chemical Synthesis
Objective Division:Expanding Knowledge
Objective Group:Expanding Knowledge
Objective Field:Expanding Knowledge in the Chemical Sciences
UTAS Author:Bissember, AC (Dr Alex Bissember)
ID Code:125070
Year Published:2018
Web of Science® Times Cited:12
Deposited By:Chemistry
Deposited On:2018-03-27
Last Modified:2019-03-06
Downloads:0

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