Boron-mediated modular assembly of tetrasubstituted alkenes.

ABSTRACT: Alkenes are a central part of organic chemistry^1-3. However, although most alkenes are easy to prepare, the controlled synthesis of tetrasubstituted alkenes, those with four groups around the central C=C bond, remains challenging^1-5. Here we report the boron-mediated assembly of tetrasubstituted alkenes with complete control of the double-bond geometry. The migrating group and electrophile add syn across the alkyne. Mild oxidation leads to intermediate borinic esters⁶, which can be isolated and purified or reacted directly in a range of transformations, including cross-couplings and homologation reactions. In particular, subjecting the intermediate borinic esters to Zweifel^7,8 olefination conditions can give either retention or inversion of the d

SUBMITTER: Wei L 

PROVIDER: S-EPMC12286843 | biostudies-literature | 2025 Jul

REPOSITORIES: biostudies-literature