A new chiral phenomenon of orientational chirality, its synthetic control and computational study.

ABSTRACT: A new type of chirality, orientational chirality, consisting of a tetrahedron center and a remotely anchored blocker, has been discovered. The key structural element of this chirality is characterized by multiple orientations directed by a through-space functional group. The multi-step synthesis of orientational chiral targets was conducted by taking advantage of asymmetric nucleophilic addition, Suzuki-Miyaura cross-coupling and Sonogashira coupling. An unprecedented catalytic species showing a five-membered ring consisting of C (sp²)-Br-Pd-C (sp²) bonds was isolated during performing Suzuki-Miyaura cross-coupling. X-ray diffraction analysis confirmed the species structure and absolute configuration of chiral orientation products. Based on X-ray structures, a model w

SUBMITTER: Jin S 

PROVIDER: S-EPMC9850238 | biostudies-literature | 2022

REPOSITORIES: biostudies-literature