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Synthesis 2017; 49(14): 3118-3125
DOI: 10.1055/s-0036-1588787
DOI: 10.1055/s-0036-1588787
paper
Asymmetric Organocatalytic Michael Addition–Cyclization Cascade of Cyclopentane-1,2-dione with Substituted α,β-Unsaturated Aldehydes
Supported by: The authors thank the following agencies for financial support: Estonian Ministry of Education and Research (IUT 19-32) (IUT 19-9) (IUT 23-7) (PUT 692)Supported by: Tallinn University of Technology (B25)
Supported by: European Social Fund (DoRa)
Supported by: EU European Regional Development Fund (3.2.0101.08-0017)
Supported by: Centre of Excellence in Molecular Cell Engineering (2014-2020.4.01.15-0013)
Supported by: Academy of Finland (263256) (265328) (292746)
Further Information
Publication History
Received: 07 February 2017
Accepted after revision: 17 March 2017
Publication Date:
18 April 2017 (online)
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.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1588787.
- Supporting Information
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