Catalytic asymmetric tandem Heck/Sonogashira reaction enabling access to versatile chiral bridged ring scaffolds.

ABSTRACT: Bridged-ring scaffolds are prevalent in numerous natural products and pharmaceuticals. However, achieving enantioselective construction of these architectures presents a significant challenge, due to the considerable structural strain of the products and the presence of multiple stereocenters. Herein, we report a Pd/Cu co-catalyzed substrate-dependent enantiodivergent tandem Heck/Sonogashira reaction for the synthesis of alkyne-tethered (R,S,S)-bicyclo[3.2.1]octenes and (S,R,R)-benzo-bicyclo[3.2.1]octanes, each featuring one quaternary and two adjacent tertiary stereocenters. Intramolecular cyclization of the resultant bridged-ring skeletons facilitates the stereospecific synthesis of rigid chiral tricyclodecanes and tetracyclotetradecanes. The alkene, alkyne and ester motifs within bicycl

SUBMITTER: Zhong J 

PROVIDER: S-EPMC12728211 | biostudies-literature | 2025 Dec

REPOSITORIES: biostudies-literature