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

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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… Click to show full abstract

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.

Keywords: michael; cyclopentane; michael addition; organocatalytic michael; addition cyclization; asymmetric organocatalytic

Journal Title: Synthesis
Year Published: 2017

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