Controlled semi‐Pinacol rearrangement on a strained ring: Efficient access to multi‐substituted cyclopropanes by group migration strategy
Chinese Chemical Letters(2023)
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 version of SPR wherein migration to a non-benzylic bulky tertiary carbo-cation is realized with promising enantiocontrol.
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Key words
Cyclopropene α-carbinols,Electrophile addition,Semi-Pinacol rearrangement,Cyclopropane
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