and the Rotational Kinetics of the Axially Chiral C-N Bond
Shishi Lin Dasheng Leow Kuo‐Wei Huang Prof. Dr. Choon‐Hong Tan Prof. Dr.
Chemistry An Asian Journal,2009, 4, 1741–1744
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 N‐substituted 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.
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