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Kinetic resolution of 2-hydroxy-2-aryl-ethylphosphonates by a non-enzymatic acylation catalyst
KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry. Uppsala University.ORCID iD: 0000-0001-6782-6622
2014 (English)In: Tetrahedron, ISSN 0040-4020, E-ISSN 1464-5416, Vol. 70, no 24, 3807-3811 p.Article in journal (Refereed) Published
Abstract [en]

Optically pure hydroxyphosphonates are widely used as derivatizable compounds that can be incorporated into a variety of synthetic strategies for the preparation of other high value organic products. A non-enzymatic kinetic resolution procedure to obtain chiral 2-hydroxy-2-arylethylphosphonates from the easily available racemic counterparts is described. A range of 2-hydroxy-2-arylethylphosphonates was efficiently resolved employing a planar-chiral DMAP derived catalyst with good selectivities (up to S=68). The chiral hydroxyphosphonates were isolated in good yields and high enantiomeric excess (>94% ee).

Place, publisher, year, edition, pages
Elsevier, 2014. Vol. 70, no 24, 3807-3811 p.
Keyword [en]
2-Hydroxy-2-arylethylphosphonates, Non-enzymatic kinetic resolution, Planar chiral DMAP derivative catalyst
National Category
Organic Chemistry
Identifiers
URN: urn:nbn:se:kth:diva-147409DOI: 10.1016/j.tet.2014.03.102ISI: 000336710200010Scopus ID: 2-s2.0-84899991575OAI: oai:DiVA.org:kth-147409DiVA: diva2:731620
Funder
Swedish Research Council, 621-2009-4018
Note

QC 20140702

Available from: 2014-07-02 Created: 2014-06-27 Last updated: 2017-12-05Bibliographically approved

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Dinér, Peter

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