Asymmetric Catalytic [3 + 3] Annulations of Unmodified Morita-Baylis-Hillman Alcohols to Construct Diverse Heterobicyclic [4.3.0] Skeletons.

ABSTRACT: Due to the high C-OH bond dissociation energy and unpredictable site selectivity, the direct application of unmodified cyclic MBH alcohols presents significant challenges. Herein, we described a series of highly enantioselective β,β'-site-selective annulations of unmodified cyclic MBH alcohols, which provides a strategy for the asymmetric construction of structurally diverse chiral heterobicyclic [4.3.0] skeletons. Azabicyclic, oxobicyclic, and thiabicyclic [4.3.0] skeletons could be synthesized with excellent stereoselectivities through this general platform. Catalyst rather than substrate-controlled feature renders the reaction minimal sensitivity to substrate properties. Furthermore, the synthetic potential of this method was underscored by facile access to various pharmaceutically acti

SUBMITTER: Zhang Y 

PROVIDER: S-EPMC12569669 | biostudies-literature | 2025 Oct

REPOSITORIES: biostudies-literature