title: An unprecedented chemospecific and stereoselective tandem nucleophilic addition/cycloaddition reaction of nucleophilic carbenes with ketenimines.
abstract: The first study of the reaction between nucleophilic carbenes and ketenimines is reported. The interaction of thiazole and benzothiazole carbenes with ketenimines proceeded in a chemospecific and stereoselective manner to produce thiazole- and benzothiazole-spiro-pyrrole derivatives generally in good yields. The reaction was proposed to proceed via a tandem nucleophilic addition of carbene to the C=N bond of ketenimine followed by a stepwise [3+2] cycloaddition of the 1,3-dipolar intermediate with the C=C bond of ketenimine. This reaction provides a powerful protocol for the construction of novel polyfunctional thiazole-spiro-pyrrole or benzothiazole-spiro-pyrrole compounds that are not readily accessible by other methods.
authors.affiliation: College of Chemistry, Beijing Normal University, Beijing, 100875, China. ycheng2@bnu.edu.cn
authors.forename: Ying
authors.initials: Y
authors.lastname: Cheng
authors.forename: Yang-Guang
authors.initials: YG
authors.lastname: Ma
authors.forename: Xiao-Rong
authors.initials: XR
authors.lastname: Wang
authors.forename: Jun-Ming
authors.initials: JM
authors.lastname: Mo