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Synfacts 2008(7): 0762-0762  
DOI: 10.1055/s-2008-1077822
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Tetrahydropyrans via a Domino Aldol-Acetalization Reaction

Contributor(s): Benjamin List, Kristina Zumbansen
D. Hazelard, H. Ishikawa, D. Hashizume, H. Koshino, Y. Hayashi*
Tokyo University of Science and RIKEN, Saitama, Japan
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Publication History

Publication Date:
20 June 2008 (online)

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Significance

An enantioselective synthesis of tetrahydropyrans via domino proline-mediated
aldol reaction-intramolecular acetal formation is presented. Excellent results were obtained using electron-deficient aldehydes and 10 mol% of proline, whereas using aryl aldehydes without strong electron-withdrawing groups 30 mol% of the catalyst and three equivalents of aqueous tetrahydro-2H-pyran-2,6-diol were necessary to observe high enantioselectivities and good yields. Relative and absolute configuration of the products have been determined.