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Benzyne-mediated trichloromethylation of chiral oxazolines

Author:
HuangX. Huang and W. Zhao contributed equally to this work., Xin, Zhao, Weizhao, Chen, De-Li, Zhan, Yaling, Zeng, Tingting, Jin, Huiquan, Peng, Bo
Source:
Chemical communications 2019 v.55 no.14 pp. 2070-2073
ISSN:
1364-548X
Subject:
Lewis acids, chemical communication, chloroform, deprotonation
Abstract:
A three-component reaction between benzyne, oxazolines and chloroform was developed for the synthesis of trichloromethylated chiral oxazolidines. Benzyne not only serves as an electrophile towards oxazolines but also acts as a base for the deprotonation of chloroform. The dual functions of benzyne enable the trichloromethylation of chiral oxazolines and thus construct chiral N,O-quaternary stereocenters.
Agid:
6308112