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Synfacts 2006(9): 0931-0931  
DOI: 10.1055/s-2006-949236
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

2,3,4,6-Tetrasubstituted Tetrahydropyrans by Prins-Type Cyclization

Contributor(s): Hisashi Yamamoto, Matthew B. Boxer
U. Biermann, A. Lützen, J. O. Metzger*
University of Oldenburg, Germany
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Publication History

Publication Date:
23 August 2006 (online)

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Significance

Highly substituted tetrahydropyran molecules are important compounds for biological activity. The authors have extended their previous work on Prins-type cyclizations by using higher-order aldehydes (previously used formaldehyde) and commercially available chiral homoallylic alcohol methyl ricinoleate. Various aldehydes proved to be viable substrates, including hexanal, isobutyraldehyde, pivaldehyde and benzaldehyde. High diastereoselectivities were obtained (dr range from 60:27:9:4 to 96:2:2) for this reaction in which three new stereocenters are formed.