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Enantioselective Protonation of Itaconimides with Thiols and the Rotational Kinetics of the Axially Chiral CN Bond
Author(s) -
Lin Shishi,
Leow Dasheng,
Huang KuoWei,
Tan ChoonHong
Publication year - 2009
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.200900331
Subject(s) - protonation , enantioselective synthesis , chemistry , bicyclic molecule , conjugate , medicinal chemistry , catalysis , guanidine , stereochemistry , organic chemistry , ion , mathematical analysis , mathematics
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 CN axis of N ‐2‐ tert ‐butyl phenylitaconimide is also studied, both experimentally and computationally.