6533b872fe1ef96bd12d2d90

RESEARCH PRODUCT

Asymmetric Organocatalytic Michael Addition–Cyclization Cascade of Cyclopentane-1,2-dione with Substituted α,β-Unsaturated Aldehydes

Sandra KaabelSandra KaabelGert PreegelKari RissanenMargus LoppIvar JärvingEstelle Silm

subject

Bicyclic molecule010405 organic chemistryDihydropyranOrganic Chemistry010402 general chemistry01 natural sciencesCatalysis0104 chemical scienceschemistry.chemical_compoundchemistryCascade reactionCascadeOrganocatalysisMichael reactionOrganic chemistryCyclopentane

description

An asymmetric organocatalytic Michael addition–cyclization cascade reaction has been developed using cyclopentane-1,2-dione as a Michael donor and α,β-unsaturated aldehydes as Michael acceptors. Bicyclic hemiacetals were obtained in excellent yields and enantioselectivities. On the basis of the results, a one-pot reaction has been developed to obtain chiral 3-substituted cyclopentane-1,2-diones and substituted dihydropyrans in good yields and excellent enantioselectivity.

yearjournalcountryeditionlanguage
2017-04-18Synthesis
https://doi.org/10.1055/s-0036-1588787