Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000131.xml
Synfacts 2006(9): 0931-0931
DOI: 10.1055/s-2006-949236
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
U. Biermann, A. Lützen, J. O. Metzger*
University of Oldenburg, Germany
Further Information
Publication History
Publication Date:
23 August 2006 (online)
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.