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

Qian, D, Chen, M, Bissember, AC ORCID: 0000-0001-5515-2878 and Sun, J 2018 , 'Counterion-induced asymmetric control in ring-opening of azetidiniums: facile access to chiral amines' , Angewandte Chemie, vol. 57, no. 14 , pp. 3763-3766 , doi: 10.1002/anie.201712395.

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Abstract

Counterion-induced stereocontrol is a powerful tool in organic synthesis. However, such enantiocontrol on tetrahedral ammonium cations remains challenging. Described here isthe first example of using chiral anion phase-transfer catalysis to achieve intermolecular ring-opening of azetidiniums with excellent enantioselectivity (up to 97% ee). Precise controlover 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 Type: Article
Authors/Creators:Qian, D and Chen, M and Bissember, AC and Sun, J
Keywords: organocatalysis, phase-transfer catalysis, azetidiniums
Journal or Publication Title: Angewandte Chemie
Publisher: Wiley-V C H Verlag Gmbh
ISSN: 1433-7851
DOI / ID Number: 10.1002/anie.201712395
Copyright Information:

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

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