Asymmetric Hydroacylation Involving Alkene Isomerization for the Construction of C<sub>3</sub>‐Chirogenic Center
Chong Liu, Jing Yuan, Zhenfeng Zhang, Ilya D. Gridnev, Wanbin Zhang
Abstract
Abstract A new transformation pattern for enantioselective intramolecular hydroacylation has been developed involving an alkene isomerization strategy. Proceeding through a five‐membered rhodacycle intermediate, 3‐enals were converted to C 3 ‐ or C 3 ,C 5 ‐chirogenic cyclopentanones with satisfactory yields, diastereoselectivities, and enantioselectivities. A catalytic cycle has been theoretically calculated and the origin of the stereoselection is rationally explained.
Topics & Concepts
HydroacylationAlkeneIsomerizationIntramolecular forceEnantioselective synthesisChemistryCatalysisCenter (category theory)StereochemistryOrganic chemistryAldehydeCrystallographyCatalytic C–H Functionalization MethodsAsymmetric Hydrogenation and CatalysisSynthetic Organic Chemistry Methods