Stereoselective synthesis of enantiopure cyclic α‐aminophosphonic acids: Direct observation of inversion at phosphorus in phosphonate ester silyldealkylation by bromotrimethylsilane

descriptionPublicationkeyboard_double_arrow_right Article 01 Sep 2008 English Publisher:WileyJournal:Heteroatom Chemistry, volume 19, pages 575-582 (issn: 1042-7163, eissn: 1098-1071,

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Authors: Vladimir A. Alfonsov; Charles E. McKenna; Evgenia V. Bayandina; Boris A. Kashemirov; Liliya N. Yarmieva; Lyudmila N. Punegova; Olga N. Kataeva;

doi: 10.1002/hc.20480

Stereoselective synthesis of enantiopure cyclic α‐aminophosphonic acids: Direct observation of inversion at phosphorus in phosphonate ester silyldealkylation by bromotrimethylsilane

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Abstract

AbstractThe paper describes a simple, direct synthesis of enantiopure cyclic α‐aminophosphonic acids on the basis of silyldealkylation and followed by hydrolysis of the parent diastereoisomeric cyclic 1,4,2‐oxazaphosphorines, which have been obtained by intramolecular stereospecific nucleophilic addition of phosphites to imines. In this approach, the high diastereoselectivity of the stereocontrolling penultimate step is preserved by conversion of the intermediate ester to the final phosphonic acid under very mild, nonracemizing conditions. © 2008 Wiley Periodicals, Inc. Heteroatom Chem 19:575–582, 2008; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.20480

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