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Synfacts 2005(0): 0060-0060  
DOI: 10.1055/s-2005-869941
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Scandium(III) Triflate-Catalyzed Stereoselec­-tive Synthesis of Tetrahydropyran-4-ones

Contributor(s): Mark Lautens, Josephine Yuen
W. J. Morris, D. W. Custar, K. A. Scheidt*
Northwestern University, Evanston, USA
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Publication History

Publication Date:
20 July 2005 (online)

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Significance

Tetrahydropyran-4-ones were synthesized with high diastereoselectivity using a scandium(III) triflate-catalyzed cyclization between an aldehyde and β-hydroxydioxinones. Either the dioxinone intermediate could be isolated or direct addition of an alkoxide would generate the 2,6-disubstituted tetrahydropyran-4-one. Aromatic and aliphatic substituents including α-branched aldehydes were tolerated. A variety of substituents on the dioxinone were also explored.