Synthesis 2006(18): 3111-3121  
DOI: 10.1055/s-2006-950194
PAPER
© Georg Thieme Verlag Stuttgart · New York

Enantio- and Diastereoselective Synthesis of Tetrahydrofurochromenes by Sequential Asymmetric Homoaldol Reaction and a Mukaiyama-Type Tetrahydrofuran­ Cyclization

Astrid Brüns, Birgit Wibbeling, Roland Fröhlich, Dieter Hoppe*
Westfälische Wilhelms-Universität Münster, Organisch-Chemisches Institut, Corrensstraße 40, 48149 Münster, Germany
Fax: +49(251)8336531; e-Mail: dhoppe@uni-muenster.de;
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Publication History

Received 10 April 2006
Publication Date:
15 August 2006 (online)

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Abstract

Herein, we report on a flexible strategy for the stereoselective construction of highly substituted tetrahydrofurochromene derivatives by Mukaiyama-type cyclizations of enantioenriched enol carbamates with O-protected salicylaldehydes. The chromenes are generated as pure diastereomers and under complete chirality transfer.