Divergent asymmetric synthesis of 3,5-disubstituted piperidines.
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
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.
Research subject Organic Chemistry
IdentifiersURN: urn:nbn:se:su:diva-20419DOI: 10.1021/jo0615091ISI: 000241053000042PubMedID: 17025320OAI: oai:DiVA.org:su-20419DiVA: diva2:186945
FunderSwedish Research Council