Rhodium-Catalyzed Diastereo- and Enantioselective Divergent Annulations between Cyclobutanones and 1,5-Enynes: Rapid Construction of Complex C(sp³)-Rich Scaffolds.

ABSTRACT: Given the emerging demand to "escape from flatland" for drug discovery, synthetic methods that can efficiently construct complex three-dimensional structures with multi-stereocenters become increasingly valuable. Here, we describe the development of Rh(I)-catalyzed intramolecular annulations between cyclobutanones and 1,5-enyne groups to construct complex C(sp³)-rich scaffolds. Divergent reactivities are realized with different catalysts, and excellent diastereo- and enantioselectivity have been achieved. The use of (R)-H₈-binap as the ligand favors forming the bis-bicyclic scaffolds with multiple quaternary stereocenters, while the (R)-segphos ligand prefers to generate the tetrahydro-azapinone products. Owing to the versatile reactivity of ketone moiet

SUBMITTER: Hou SH 

PROVIDER: S-EPMC10630065 | biostudies-literature | 2022 Dec

REPOSITORIES: biostudies-literature