中国化学快报(英文版)2024,Vol.35Issue(9) :135-139.DOI:10.1016/j.cclet.2023.109447

Controlled semi-Pinacol rearrangement on a strained ring:Efficient access to multi-substituted cyclopropanes by group migration strategy

Wenyu Gao Liming Zhang Chuang Zhao Lixiang Liu Xingran Yang Jinbo Zhao
中国化学快报(英文版)2024,Vol.35Issue(9) :135-139.DOI:10.1016/j.cclet.2023.109447

Controlled semi-Pinacol rearrangement on a strained ring:Efficient access to multi-substituted cyclopropanes by group migration strategy

Wenyu Gao 1Liming Zhang 1Chuang Zhao 1Lixiang Liu 1Xingran Yang 1Jinbo Zhao1
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作者信息

  • 1. Faulty of Chemistry and Life Science,Changchun University of Technology,Changchun 130012,China
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Abstract

We describe a versatile electrophile addition/SPR sequence of readily available cyclopropyl carbinols that affords multi-substituted carbonylated cyclopropanes with high stereo-fidelity.This approach tolerates various heteroatom electrophiles,migration of carbon moiety of all possible hybridization states,facile ring reorganization and natural compound valorization.The examples represent an unprecedented ver-sion of SPR wherein migration to a non-benzylic bulky tertiary carbo-cation is realized with promising enantiocontrol.

Key words

Cyclopropene α-carbinols/Electrophile addition/Semi-Pinacol rearrangement/Cyclopropane

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出版年

2024
中国化学快报(英文版)
中国化学会

中国化学快报(英文版)

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影响因子:0.771
ISSN:1001-8417
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