Construction of Multi-Substituted Strained Carbocycles Enabledby Enantioselective Reduction with Sodium Borohydride

Abstract

The stereoselective reduction of strained molecules and subsequent synthetic transformations provide an efficient strategy to access multi-substituted carbocycles. These carbocycles are important structural skeletons in natural products and bioactive molecules. We report here a Luche-type enantioselective reduction of cyclobutenones and strained-ring fused cyclic imides. This process utilizes the catalysis of Sc–N,N’-dioxide ligand complex and NaBH₄ as reductant. Moreover, the developed methodology is applicable to the strained olefins, which are not tolerated under metal hydride conditions.

Keywords

Enantioselective reduction / Cyclic imide / Desymmetrization / Scandium / Strained molecules

RIGHTS & PERMISSIONS

2025 SIOC, CAS, Shanghai, & WILEY-VCH GmbH