Enantioselective protonation of itaconimides with thiols and the rotational kinetics of the axially chiral C-N bond.
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.
Lin
Shishi
S
Department of Chemistry, National University of Singapore (NUS), 3 Science Drive 3, Singapore.
Leow
Dasheng
D
Huang
Kuo-Wei
KW
Tan
Choon-Hong
CH
D002384:Catalysis; D019791:Guanidine / Q000737:chemistry*; D007094:Imides / Q000737:chemistry*; D011522:Protons; D013386:Succinates / Q000737:chemistry*; D013438:Sulfhydryl Compounds / Q000737:chemistry*
D007094:Imides; D011522:Protons; D013386:Succinates; D013438:Sulfhydryl Compounds; D019791:Guanidine; C005229:itaconic acid