Facile Access to Cyclopropylboronates via Stereospecific Deborylative Cyclization: A Leaving Group‐Assisted Activation of Geminal Diborons DOI
Xinyi Chen,

Feng‐Chen Gao,

Peng‐Fei Ning

et al.

Angewandte Chemie, Journal Year: 2023, Volume and Issue: 135(21)

Published: March 24, 2023

Abstract Herein we reported a transition metal‐free deborylative cyclization strategy, based on which two routes have been developed, generating racemic and enantioenriched cyclopropylboronates. The of geminal‐bis(boronates) bearing leaving group was highly diastereoselective, tolerating few functional groups applicable to heterocycles. When optically active epoxides were used as the starting materials, cyclopropylboronates could be efficiently prepared with >99 % stereospecificity. Mechanistic studies showed that at γ ‐position played crucial role significantly promoted activation gem ‐diboron moiety.

Language: Английский

Facile Access to Cyclopropylboronates via Stereospecific Deborylative Cyclization: A Leaving Group‐Assisted Activation of Geminal Diborons DOI
Xinyi Chen,

Feng‐Chen Gao,

Peng‐Fei Ning

et al.

Angewandte Chemie, Journal Year: 2023, Volume and Issue: 135(21)

Published: March 24, 2023

Abstract Herein we reported a transition metal‐free deborylative cyclization strategy, based on which two routes have been developed, generating racemic and enantioenriched cyclopropylboronates. The of geminal‐bis(boronates) bearing leaving group was highly diastereoselective, tolerating few functional groups applicable to heterocycles. When optically active epoxides were used as the starting materials, cyclopropylboronates could be efficiently prepared with >99 % stereospecificity. Mechanistic studies showed that at γ ‐position played crucial role significantly promoted activation gem ‐diboron moiety.

Language: Английский

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