Synthesis of alkenyl boronates through stereoselective vinylene homologation of organoboronates.

ABSTRACT: Matteson homologation of organoboronates is an attractive approach for constructing aliphatic carbon chains via iterative insertion of carbenoids. However, the corresponding homologation that can introduce alkene moieties to molecular backbones remains elusive. Here we report the development of a stereoselective vinylene homologation reaction of various alkyl and aryl boronates. The reaction proceeds through diastereoselective consecutive insertion of a silyl- and an alkoxy-substituted carbenoid, followed by a Peterson-type elimination. A diverse range of alkenyl boronates can be formed in good yield and with good to excellent trans selectivity. Density functional theory calculations reveal the origin of diastereoselectivity in carbenoid insertion and how Lewis acids with different

SUBMITTER: Chen M 

PROVIDER: S-EPMC12352499 | biostudies-literature | 2024 Mar

REPOSITORIES: biostudies-literature