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|Title:||Origin of asymmetric induction in bicyclic guanidine-catalyzed thio-Michael reaction: A bifunctional mode of Lewis acid-Brønsted acid activation|
|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|
|Appears in Collections:||Staff Publications|
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