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