Synthetic and Computational Study of the Enantioselective [3+2]-Cycloaddition of Chromones with MBH Carbonates
Ling Meng1,2,3,4, Heyang Liu3, Zhenyang Lin2
1Department of Chemistry, Hong Kong Baptist University, Hong Kong 999077, China.
Abstract:
Highly efficient and straightforward access to enantioenriched five-membered ring-fused chromanones is developed via [3+2]-cycloaddition of 3-cyanochromones with Morita-Baylis-Hillman carbonates. Densely functionalized chiral cyclopenta[b]chromanones with three continuous quaternary and tertiary stereogenic carbon centers were obtained in high yields with high ee and dr (≤97% yield, 97% ee, and >20:1 dr). Moreover, density functional theory calculations have been carried out to investigate the mechanism and regio- and diastereoselectivity of the reaction.
More Related Videos
Related Concept Videos
Regioselectivity and Stereochemistry of Hydroboration
Hydroboration proceeds in a concerted fashion with the attack of borane on the π bond, giving a cyclic four-centered transition state. The –BH2 group is bonded to the less substituted carbon and –H to the more substituted carbon. The concerted nature requires the simultaneous addition of –H and –BH2 across the same face of the alkene giving syn...
Formation of Halohydrin from Alkenes
Prochirality
Cycloaddition Reactions: Overview
Regioselectivity of Electrophilic Additions to Alkenes: Markovnikov's Rule
The hydrohalogenation of an unsymmetrical alkene can yield two haloalkane products, depending on which vinylic carbon takes up the halogen. However, one product usually predominates, where hydrogen adds to the vinylic carbon bearing the...
Radical Anti-Markovnikov Addition to Alkenes: Overview


