N-Heterocyclic carbenes (NHCs) are a class of imidazolium-derived compounds frequently exploited for their high nucleophilicity and remarkable catalytic power. It was shown by Castedo, et al. that reactions of chiral β-ethanolamines with in situ-generated dichlorocarbene resulted in asymmetric epoxides in high enantiomeric excess. Here, the electrophilicity of NHCs is exploited to accomplish the conversion of α-amino alcohols to epoxides catalytically. It was demonstrated that under basic conditions, 1,3-di(mesityl)imidazolin-2-ylidine (H2IMes) can convert N,N-dimethylphenylalanol to 2-benzyloxirane. However, the high nucleophilicity of H2IMes requires reaction conditions in which electrophilic addition to the carbene resulting in non-reactive adducts is precluded.

N-Heterocyclic carbene-catalyzed conversion of α-amino alcohols to their corresponding epoxides

253rd National Meeting (2017)

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.