Stereoselective Formation of Trisubstituted Vinyl Boronate Esters by the Acid-mediated Elimination of α-hydroxyboronate Esters

Overview

Journal J Org Chem

Publisher American Chemical Society

Specialty Chemistry

Date 2014 Jun 11

PMID 24915498

Citations 9

Authors

Weiye Guan

Alicia K Michael

Melissa L McIntosh

Liza Koren-Selfridge

John P Scott

Timothy B Clark

Affiliations

Soon will be listed here.

Abstract

The copper-catalyzed diboration of ketones followed by an acid-catalyzed elimination leads to the formation of 1,1-disubstituted and trisubstituted vinyl boronate esters with moderate to good yields and selectivity. Addition of tosic acid to the crude diboration products provides the corresponding vinyl boronate esters upon elimination. The trisubstituted vinyl boronate esters are formed as the (Z)-olefin isomer, which was established by subjecting the products to a Suzuki-Miyaura coupling reaction to obtain alkenes of known geometry.

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