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Synthesis 2014; 46(09): 1261-1269
DOI: 10.1055/s-0033-1340826
paper
© Georg Thieme Verlag Stuttgart · New York

Asymmetric Synthesis of Functionalized Dihydro- and Tetrahydropyrans via an Organocatalytic Domino Michael–Hemiacetalization Reaction

Gregor Urbanietz
Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany   Fax: +49(241)8092127   Email: enders@rwth-aachen.de
,
Iuliana Atodiresei
Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany   Fax: +49(241)8092127   Email: enders@rwth-aachen.de
,
Dieter Enders*
Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany   Fax: +49(241)8092127   Email: enders@rwth-aachen.de
› Author Affiliations
Further Information

Publication History

Received: 22 January 2014

Accepted: 24 January 2014

Publication Date:
18 February 2014 (online)

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Abstract

Starting from α-hydroxymethyl nitroalkenes and various 1,3-dicarbonyl compounds, a one-pot organocatalyzed diastereo- and enantioselective synthesis of polyfunctionalized dihydro- and tetrahydropyran derivatives via a domino Michael-hemiacetalization sequence is reported. The title compounds bearing a variety of functional groups can be synthesized in this way in good yields (59–91%) and with moderate to excellent diastereoselectivities (26–98% de) and enantioselectivities (71–99% ee).

Key words

organocatalysis - domino reaction - one-pot reaction - tetrahydropyrans - hydrogen bonding

Supporting Information

    for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
  • Supporting Information
 

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