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Divergent asymmetric synthesis of 3,5-disubstituted piperidines.
Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.ORCID-id: 0000-0001-7975-4582
Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi. (Bäckvall)
Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi. (Bäckvall)
Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
2006 (engelsk)Inngår i: Journal of Organic Chemistry, ISSN 0022-3263, E-ISSN 1520-6904, Vol. 71, nr 21, s. 8256-60Artikkel i tidsskrift (Fagfellevurdert) 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.

sted, utgiver, år, opplag, sider
2006. Vol. 71, nr 21, s. 8256-60
HSV kategori
Forskningsprogram
organisk kemi
Identifikatorer
URN: urn:nbn:se:su:diva-20419DOI: 10.1021/jo0615091ISI: 000241053000042PubMedID: 17025320OAI: oai:DiVA.org:su-20419DiVA, id: diva2:186945
Forskningsfinansiär
Swedish Research CouncilTilgjengelig fra: 2007-03-28 Laget: 2007-03-28 Sist oppdatert: 2018-02-12bibliografisk kontrollert

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Olofsson, BeritBogár, KrisztiánBäckvall, Jan-Erling
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