Please use this identifier to cite or link to this item: https://doi.org/10.1021/jo301158c
Title: Origin of asymmetric induction in bicyclic guanidine-catalyzed thio-Michael reaction: A bifunctional mode of Lewis acid-Brønsted acid activation
Authors: Cho, B.
Tan, C.-H. 
Wong, M.W. 
Issue Date: 3-Aug-2012
Citation: Cho, B., Tan, C.-H., Wong, M.W. (2012-08-03). Origin of asymmetric induction in bicyclic guanidine-catalyzed thio-Michael reaction: A bifunctional mode of Lewis acid-Brønsted acid activation. Journal of Organic Chemistry 77 (15) : 6553-6562. ScholarBank@NUS Repository. https://doi.org/10.1021/jo301158c
Abstract: In addition to a bifunctional Brønsted acid activation mode, an unconventional bifunctional mode of Lewis and Brønsted acid activations was revealed in a DFT study of bicyclic guanidine-catalyzed thio-Michael reaction. This activation mode provides an alternate reaction pathway for the C-S bond forming step and influences the final stereochemical outcome. The calculated turnover frequencies of the R- and S-products, based on the energetic span model, are in good accord with the observed high stereoselectivity toward the S-product. © 2012 American Chemical Society.
Source Title: Journal of Organic Chemistry
URI: http://scholarbank.nus.edu.sg/handle/10635/94455
ISSN: 00223263
DOI: 10.1021/jo301158c
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