Please use this identifier to cite or link to this item: https://doi.org/10.1002/asia.200900331
Title: Enantioselective protonation of itaconimides with thiols and the rotational kinetics of the axially chiral C-N bond
Authors: Lin, S.
Leow, D.
Huang, K.-W. 
Tan, C.-H. 
Keywords: Asymmetric catalysis
Atropisomerism
Guanidines
Organocatalysis
Protonation
Issue Date: 2-Nov-2009
Citation: Lin, S., Leow, D., Huang, K.-W., Tan, C.-H. (2009-11-02). Enantioselective protonation of itaconimides with thiols and the rotational kinetics of the axially chiral C-N bond. Chemistry - An Asian Journal 4 (11) : 1741-1744. ScholarBank@NUS Repository. https://doi.org/10.1002/asia.200900331
Abstract: Bicyclic guanidines are able to catalyze the protonation reactions of 2- phthalimidoacrylates with thiols in excellent yields and enantioselectivities. The protonation reaction of itaconimides with secondary phosphine oxides is also known. Herein, the tandem conjugate addition-enantioselective protonation of Nsubstituted itaconimides with thiols catalyzed by chiral bicyclic guanidine is investigated. The rotational barrier of the C-N axis of N-2-tert-butyl phenylitaconimide is also studied, both experimentally and computationally. © 2009 Wiley-VCH Verlag GmbH & Co. KGaA.
Source Title: Chemistry - An Asian Journal
URI: http://scholarbank.nus.edu.sg/handle/10635/76107
ISSN: 18614728
DOI: 10.1002/asia.200900331
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