Please use this identifier to cite or link to this item: https://hdl.handle.net/10356/137752
Title: Access to cyclic β-amino acids by amine-catalyzed enantioselective addition of the γ-carbon atoms of α,β-unsaturated imines to enals
Authors: Luo, Guoyong
Huang, Zhijian
Zhuo, Shitian
Mou, Chengli
Wu, Jian
Jin, Zhichao
Chi, Robin Yonggui
Keywords: Science::Chemistry::Organic chemistry
Issue Date: 2019
Source: Luo, G., Huang, Z., Zhuo, S., Mou, C., Wu, J., Jin, Z., & Chi, R. Y. (2019). Access to cyclic β-amino acids by amine-catalyzed enantioselective addition of the γ-carbon atoms of α,β-unsaturated imines to enals. Angewandte Chemie International Edition, 58(48), 17189-17193. doi:10.1002/ange.201908896
Journal: Angewandte Chemie International Edition
Abstract: 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.
URI: https://hdl.handle.net/10356/137752
ISSN: 1433-7851
DOI: 10.1002/anie.201908896
Schools: School of Physical and Mathematical Sciences 
Rights: This is the peer reviewed version of the following article: Luo, G., Huang, Z., Zhuo, S., Mou, C., Wu, J., Jin, Z., & Chi, R. Y. (2019). Access to cyclic β-amino acids by amine-catalyzed enantioselective addition of the γ-carbon atoms of α,β-unsaturated imines to enals. Angewandte Chemie International Edition, 58(48), 17189-17193, which has been published in final form at https://doi.org/10.1002/anie.201908896. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Use of Self-Archived Versions.
Fulltext Permission: open
Fulltext Availability: With Fulltext
Appears in Collections:SPMS Journal Articles

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