Synlett 2014; 25(2): 280-282
DOI: 10.1055/s-0033-1340347
letter
© Georg Thieme Verlag Stuttgart · New York

A Tandem Conjugate Addition–Intramolecular Horner–Wadsworth–Emmons Olefination Approach to the Synthesis of Cyclopentene[c]chroman-2-ones and Cyclopent-1-enecarboxylates

Dariusz Deredas
a   Institute of Organic Chemistry, Technical University (Politechnika), Żeromskiego 116, 90-924 Łódź, Poland   Fax: +48(42)6365530   Email: henkrawc@p.lodz.pl
,
Krzysztof Huben
a   Institute of Organic Chemistry, Technical University (Politechnika), Żeromskiego 116, 90-924 Łódź, Poland   Fax: +48(42)6365530   Email: henkrawc@p.lodz.pl
,
Waldemar Maniukiewicz
b   Institute of General and Ecological Chemistry, Technical University (Politechnika), Żeromskiego 116, 90-924 Łódź, Poland
,
Henryk Krawczyk*
a   Institute of Organic Chemistry, Technical University (Politechnika), Żeromskiego 116, 90-924 Łódź, Poland   Fax: +48(42)6365530   Email: henkrawc@p.lodz.pl
› Author Affiliations
Further Information

Publication History

Received: 25 October 2013

Accepted after revision: 09 November 2013

Publication Date:
06 December 2013 (online)


Abstract

A strategically new approach to cyclopentene[c]chroman-2-ones and cyclopent-1-enecarboxylates by tandem Michael–Horner–Wadsworth–Emmons reaction of 2,5-hexanedione with 3-(diethoxyphosphoryl)coumarins is described. The products were obtained as single diastereoisomers in high yields.

Supporting Information

Primary Data

 
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  • 8 Crystallographic data (excluding structure factors) for the structure reported herein have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication CCDC 966779. Copies of the data can be obtained free of charge on application to The Director, CCDC, 12 Union Road, Cambridge CB2 1EZ, UK. Any request should be accompanied by a full literature citation.