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Home
Research Domains
Chemical Sciences
Organic Chemistry
Organic Chemical Synthesis
Diastereoselective Synthesis Of Cyclopropyl Diboronates Via 1,2-boronate Rearrangement.

Home
Research Domains
Chemical Sciences
Organic Chemistry
Organic Chemical Synthesis
Diastereoselective Synthesis Of Cyclopropyl Diboronates Via 1,2-boronate Rearrangement.

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

Keyi Huyan¹, Shiqin Chen¹, Wanxiang Zhao¹

¹State Key Laboratory of Chemo and Biosensing, College of Chemistry and Chemical Engineering, Hunan University, Changsha, Hunan, 410082, P.R. China.

Angewandte Chemie (International Ed. in English)

|June 12, 2025

View abstract on PubMed

Summary

This summary is machine-generated.

This study introduces an efficient method for synthesizing cyclopropyl diboronates using gem-bis(boronates) and thianthrenium salts. This approach enables the scalable and stereocontrolled creation of diverse polysubstituted cyclopropanes for various applications.

Keywords:

1,2‐Boronate migration Boron Cyclopropane Diborylalkane

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Area of Science:

Organic Chemistry
Synthetic Chemistry

Background:

Polysubstituted cyclopropanes are valuable synthetic targets.
Incorporating boron groups facilitates cyclopropane functionalization.
Existing methods for cyclopropane synthesis have limitations.

Purpose of the Study:

To develop an efficient method for constructing cyclopropyl diboronates.
To enable the synthesis of diverse polysubstituted cyclopropanes.
To provide a scalable and stereocontrolled approach to cyclopropane synthesis.

Main Methods:

Reaction of gem-bis(boronates) with thianthrenium (TT) salts.
Utilizing a 1,2-rearrangement of tetra-coordinated boron species.
Subsequent borate derivatization for stereocontrol.

Thianthrenium salt

Main Results:

Rapid construction of cyclopropyl diboronates achieved.
High efficiency in forming 1,2-disubstituted cyclopropane diboronates.
Access to highly diastereoselective polysubstituted cyclopropanes.

Conclusions:

A novel and efficient method for cyclopropane synthesis is presented.
The method allows for scalable and stereocontrolled synthesis.
This work expands possibilities for designing complex cyclopropyl structures in medicinal chemistry, materials science, and organic synthesis.