Work

Vicinal Stereocenter Construction via α-Boryl Carbanions from Borylated Cyclopropanes

Year: 2025

Type: article

Abstract: High Resolution Image Download MS PowerPoint Slide We report generation and stereocontrolled electrophilic trapping of α-boryl carbanions via the selective anionic ring-opening of stereodefined iodomethyl cyclopropylboronic esters. The strategy relies on a lithium–iodine exchange to generate borata alkene intermediates, affording vicinal tri- and tetrasubstituted boronic esters with excellent levels of diastereoselectivity after electrophilic trapping. The stereocontrol arises from conformational preferences of the boron alkylidene, driven by its unique electronic structure. This work expands the synthetic utility of α-boryl carbanions and demonstrates their potential in the stereocontrolled construction of sp 3 -rich organoboron frameworks.

Source: Journal of the American Chemical Society

DOI: 10.1021/jacs.5c12433

Authors: Tereza Pavlickova, Noam Orbach, Alexander Kaushansky, Ilan Marek

Institution: Technion – Israel Institute of Technology

Language: English

Topic: Organoboron and organosilicon chemistry

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: hybrid

Estimated APC paid: $4,500

Funders: Israel Academy of Sciences and Humanities, Israel Science Foundation, Council for Higher Education