Synthesis 2017; 49(14): 3118-3125
DOI: 10.1055/s-0036-1588787
paper
© Georg Thieme Verlag Stuttgart · New York

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

Gert Preegela, Estelle Silma, Sandra Kaabela, b, Ivar Järvinga, Kari Rissanenb, Margus Lopp*a
  • aDepartment of Chemistry and Biotechnology, Tallinn University of Technology, Akadeemia tee 15, 12618 Tallinn, Estonia   Email: margus.lopp@ttu.ee
  • bUniversity of Jyvaskyla, Department of Chemistry, Nanoscience Center, P.O. Box 35, 40014 Jyvaskyla, Finland
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 (eFirst)

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