Stereoselective Formation of Trisubstituted Vinyl Boronate Esters by the Acid-Mediated Elimination of α-Hydroxyboronate Esters

• DOI: 10.1021/jo500773t
• Publication Date: 2014-06-10T16:50:11Z
• Authors: Weiye Guan; Alicia K. Michael; Melissa L. McIntosh; Liza Koren-Selfridge; John P. Scott; Timothy B. Clark
• Keywords: Boronic acid

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