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Counterion-induced asymmetric control in ring-opening of azetidiniums: facile access to chiral amines
journal contribution
posted on 2023-05-19, 16:56 authored by Qian, D, Chen, M, Alexander BissemberAlexander Bissember, Sun, JCounterion-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.
History
Publication title
Angewandte Chemie International EditionVolume
57Issue
14Pagination
3763-3766ISSN
1433-7851Department/School
School of Natural SciencesPublisher
Wiley-V C H Verlag GmbhPlace of publication
Po Box 10 11 61, Weinheim, Germany, D-69451Rights statement
Copyright 2018 Wiley-VCH Verlag GmbH & Co. KGaA, WeinheimRepository Status
- Restricted