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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 (Associate Professor Alex Bissember) |
| ID Code: | 125070 |
| Year Published: | 2018 |
| Web of Science® Times Cited: | 20 |
| Deposited By: | Chemistry |
| Deposited On: | 2018-03-27 |
| Last Modified: | 2019-03-06 |
| Downloads: | 0 |
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