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Access to Optically Pure beta-Hydroxy Esters via Non-Enzymatic Kinetic Resolution by a Planar-Chiral DMAP Catalyst
KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi. Uppsala University, Sweden.ORCID-id: 0000-0001-6782-6622
2014 (engelsk)Inngår i: Molecules, ISSN 1420-3049, E-ISSN 1420-3049, Vol. 19, nr 9, s. 14273-14291Artikkel i tidsskrift (Fagfellevurdert) Published
Abstract [en]

The development of new approaches to obtain optically pure beta-hydroxy esters is an important area in synthetic organic chemistry since they are precursors of other high value compounds. Herein, the kinetic resolution of racemic beta-hydroxy esters using a planar-chiral DMAP derivative catalyst is presented. Following this procedure, a range of aromatic beta-hydroxy esters was obtained in excellent selectivities (up to s = 107) and high enantiomeric excess (up to 99% ee). Furthermore, the utility of the present method was demonstrated in the synthesis of (S)-3-hydroxy-N-methyl-3-phenylpropanamide, a key intermediate for bioactive molecules such as fluoxetine, tomoxetine or nisoxetine, in its enantiomerically pure form.

sted, utgiver, år, opplag, sider
2014. Vol. 19, nr 9, s. 14273-14291
Emneord [en]
non-enzymatic kinetic resolution, beta-hydroxy esters, planar-chiral DMAP catalyst, ferrocenyl catalyst
HSV kategori
Identifikatorer
URN: urn:nbn:se:kth:diva-155805DOI: 10.3390/molecules190914273ISI: 000343093100085Scopus ID: 2-s2.0-84907092007OAI: oai:DiVA.org:kth-155805DiVA, id: diva2:763049
Forskningsfinansiär
Swedish Research CouncilCarl Tryggers foundation
Merknad

QC 20141113

Tilgjengelig fra: 2014-11-13 Laget: 2014-11-13 Sist oppdatert: 2017-12-05bibliografisk kontrollert

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