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Synthesis 2016; 48(19): 3207-3216
DOI: 10.1055/s-0035-1561468
paper
Georg Thieme Verlag Stuttgart · New York

Asymmetric Synthesis of Tetrahydrobenzofurans and Annulated Dihydropyrans via Cooperative One-Pot Organo- and Silver-Catalysis

Uğur Kaya
a   Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany   Email: enders@rwth-aachen.de
,
Pankaj Chauhan
a   Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany   Email: enders@rwth-aachen.de
,
Kristina Deckers
a   Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany   Email: enders@rwth-aachen.de
,
Rakesh Puttreddy
b   Department of Chemistry, Nanoscience Center, University of Jyvaskyla, 40014 JYU, Finland
,
Kari Rissanen
b   Department of Chemistry, Nanoscience Center, University of Jyvaskyla, 40014 JYU, Finland
,
Gerhard Raabe
a   Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany   Email: enders@rwth-aachen.de
,
Dieter Enders*
a   Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany   Email: enders@rwth-aachen.de
› Author Affiliations
Further Information

Publication History

Received: 29 April 2016

Accepted: 02 May 2016

Publication Date:
23 June 2016 (online)

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In memory of Professor Jean Normant

Abstract

A low catalyst loading of a squaramide (0.5 mol%) and a silver(I) salt (1 mol%) efficiently catalyzes a one-pot asymmetric Michael addition/hydroalkoxylation reaction between 1,3-diketones and alkyne-tethered nitroalkenes. Depending on the 1,3-dicarbonyl substrate this cooperative catalytic approach opens access to tetrahydrobenzofurans or annulated dihydropyrans in moderate to excellent yields and very good to excellent enantioselectivities.

Key words

asymmetric synthesis - organocatalysis - one-pot synthesis - silver catalysis - annulation

Supporting Information

    Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0035-1561468.
  • Supporting Information
 

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