Enantioselective protonation of itaconimides with thiols and the rotational kinetics of the axially chiral C-N bond

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
Appears in Collections:	Staff Publications

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