Asymmetric synthesis of atropisomers featuring cyclobutane boronic esters facilitated by ring-strained B-ate complexes.

ABSTRACT: The strain-release-driven reactions of bicyclo[1.1.0]butanes (BCBs) have received significant attention from chemists. Notably, 1,2-migratory reactions enabled by BCB-derived B-ate complexes effectively complement the reactions initiated by common BCBs. The desired products are particularly valuable for late-stage transformations due to the presence of the C-B bond. However, asymmetric reactions mediated by BCB-derived boronate complexes have progressed slowly. In this study, we develop an asymmetric synthesis of atropisomers featuring cis-cyclobutane boronic esters facilitated by 1,2-carbon or boron migration of ring-strained B-ate complexes, achieving high enantioselectivity. The reaction is compatible with various aryl, alkenyl, alkyl boronic esters and B₂pin₂, and

SUBMITTER: Sun YW 

PROVIDER: S-EPMC11685450 | biostudies-literature | 2024 Dec

REPOSITORIES: biostudies-literature