Regio- and stereocontrolled synthesis of borylated -enynes, -enediynes and derivatives from alkenyl-1,2-bis-(boronates)

• Published in: Organic & biomolecular chemistry 2023-09, Vol.21 (37), p.7567-7571
• Main Authors: Ratanlal, Malavath, Vankudoth, Jayaram, Sharma, Gangavaram V. M, Mali, Maruti A, Carboni, Bertrand, Berrée, Fabienne, Ghosh, Subhash
• Format: Article
• ISSN: 1477-0520; 1477-0539
• DOI: 10.1039/d3ob00543g

An efficient stereo-controlled synthesis of enyne and enediyne derivatives, via sequential Suzuki-Miyaura coupling reactions from easily prepared 1-alkene-1,2-diboronic esters and alkynyl bromides, is reported. The resulting enyne boronic esters were subjected to Borono-Mannich and Suzuki coupling reactions independently to obtain α,β-unsaturated aminoester and tri-substituted olefin derivatives, respectively. Additionally, divergent syntheses of triazole and cyclopropylboronate derivatives are also reported. Herein, we present an efficient stereo-controlled synthesis of enyne and enediyne derivatives, via sequential Suzuki-Miyaura coupling reactions from easily prepared 1-alkene-1,2-diboronic esters.