Synthesis of Chiral Carbocycles via Enantioselective β,γ-Dehydrogenation.

ABSTRACT: Enantioselective dehydrogenation of prochiral C-H bonds could provide a powerful method for constructing chiral centers attached to synthetically versatile vinyl groups. Herein, we describe the realization of enantioselective β,γ-dehydrogenation of cycloalkyl amides enabled by chiral oxazoline-pyridone ligands to afford a wide range of highly elaborated carbocycles with exceptional enantioselectivity (>99% ee). Notably, the resulting chiral β,γ-unsaturated carbocycles are difficult to access via inverse electron demand Diels-Alder reaction. Through ligand control, tandem dehydrogenation and C-H olefination sequence also led to the formation of chiral β-alkylidene-γ-lactam. Remarkably, this catalyst is also compatible with complex biologically significant natural products, including diterpe

SUBMITTER: Sheng T 

PROVIDER: S-EPMC12330224 | biostudies-literature | 2024 Dec

REPOSITORIES: biostudies-literature