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

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 alpha,beta-unsaturated aminoester and tri-substituted olefin derivatives, respectively. Additionally, divergent syntheses of triazole and cyclopropylboronate derivatives are also reported.

Automated summary

An efficient stereo-controlled synthesis method using sequential Suzuki-Miyaura coupling reactions from easily prepared 1-alkene-1,2-diboronic esters and alkynyl bromides to obtain enyne and enediyne derivatives is reported. The resulting enyne boronic esters were further subjected to Borono-Mannich and Suzuki coupling reactions independently to obtain a,ss-unsaturated aminoester and tri-substituted olefin derivatives, respectively. Additionally, divergent syntheses of triazole and cyclopropylboronate derivatives were also presented.