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Divergent asymmetric synthesis of 3,5-disubstituted piperidines.
Stockholm University, Faculty of Science, Department of Organic Chemistry.
Stockholm University, Faculty of Science, Department of Organic Chemistry. (Bäckvall)
Stockholm University, Faculty of Science, Department of Organic Chemistry. (Bäckvall)
Stockholm University, Faculty of Science, Department of Organic Chemistry.
2006 (English)In: Journal of Organic Chemistry, ISSN 0022-3263, E-ISSN 1520-6904, Vol. 71, no 21, 8256-60 p.Article in journal (Refereed) Published
Abstract [en]

A divergent synthesis of various 3,5-dioxygenated piperidines with interesting pharmacological properties is described. A mixture of the achiral cis- and racemic trans-3,5-piperidine diol could be efficiently obtained from N-benzylglycinate in five steps by the use of chemoenzymatic methods. In the subsequent enzyme- and Ru-catalyzed reaction, the rac/meso diol mixture was efficiently transformed to the cis-(3R,5S)-diacetate with excellent diastereoselectivity and in high yield. Further transformations of the cis-diacetate selectively delivered the cis-piperidine diol and the cis-(3R,5S)-hydroxy acetate. Alternatively, the DYKAT could be stopped at the monoacetate stage to give the trans-(3R,5R)-hydroxy acetate.

Place, publisher, year, edition, pages
2006. Vol. 71, no 21, 8256-60 p.
National Category
Organic Chemistry
Research subject
Organic Chemistry
Identifiers
URN: urn:nbn:se:su:diva-20419DOI: 10.1021/jo0615091ISI: 000241053000042PubMedID: 17025320OAI: oai:DiVA.org:su-20419DiVA: diva2:186945
Funder
Swedish Research Council
Available from: 2007-03-28 Created: 2007-03-28 Last updated: 2015-10-14Bibliographically approved

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