Diastereoselective Synthesis of Cyclopropyl Diboronates via 1,2-Boronate Rearrangement.

Authors

Keyi Huyan, Shiqin Chen, Wanxiang Zhao

Published in

Angewandte Chemie (International ed. in English). Pages e202508322. Jun 12, 2025. Epub Jun 12, 2025.

Abstract

The preparation of polysubstituted cyclopropanes has garnered considerable attention in the field of synthetic chemistry in recent years. The introduction of boron groups into cyclopropane structures enables efficient functional modification of cyclopropane frameworks through downstream derivatization of carbon-boron bonds. Herein, we report an efficient method for the rapid construction of cyclopropyl diboronates from gem-bis(boronates) and thianthrenium (TT) salts. This transformation proceeds through a 1,2-rearrangement of tetra-coordinated boron species, delivering 1,2-disubstituted cyclopropane diboronates in high efficiency. Subsequent borate derivatization provides access to highly diastereoselective polysubstituted cyclopropanes. This method offers a scalable and stereocontrolled approach to cyclopropane synthesis and functional diversification, expanding opportunities for the design of complex cyclopropyl architectures in medicinal chemistry, materials science, and organic synthesis.

PMID:
40506394
Bibliographic data and abstract were imported from PubMed on 13 Jun 2025.

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