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

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

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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.

Cyclopropene α-carbinolsElectrophile additionSemi-Pinacol rearrangementCyclopropane

Wenyu Gao、Liming Zhang、Chuang Zhao、Lixiang Liu、Xingran Yang、Jinbo Zhao

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Faulty of Chemistry and Life Science,Changchun University of Technology,Changchun 130012,China

2024

中国化学快报(英文版)
中国化学会

中国化学快报(英文版)

CSTPCD
影响因子:0.771
ISSN:1001-8417
年,卷(期):2024.35(9)