Citation: Wenyu Gao, Liming Zhang, Chuang Zhao, Lixiang Liu, Xingran Yang, Jinbo Zhao. Controlled semi-Pinacol rearrangement on a strained ring: Efficient access to multi-substituted cyclopropanes by group migration strategy[J]. Chinese Chemical Letters, ;2024, 35(9): 109447. doi: 10.1016/j.cclet.2023.109447 shu

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

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

zhaojinbo@ccut.edu.cn

Received Date: 16 August 2023
Revised Date: 14 December 2023
Accepted Date: 20 December 2023
Available Online: 28 December 2023

Figures(6)

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 version of SPR wherein migration to a non-benzylic bulky tertiary carbo-cation is realized with promising enantiocontrol.
- Cyclopropene α-carbinols,
- Electrophile addition,
- Semi-Pinacol rearrangement,
- Cyclopropane
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