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An enantioselective synthesis of (R)-2-amino-1-hydroxyethylphosphonic acid by hydrolytic kinetic resolution of (±)-diethyl oxiranephosphonate

✍ Scribed by Peter B. Wyatt; Peter Blakskjær

Publisher
Elsevier Science
Year
1999
Tongue
French
Weight
167 KB
Volume
40
Category
Article
ISSN
0040-4039

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✦ Synopsis

_+)-Diethyl oxiranephosphonate undergoes efficient hydrolytic kinetic resolution by (R,R)-N,N'-bis(3,5-di-tertbutylsalicylidene)-l,2-cyclohexanediaminocobalt(III) acetate; opening of the resultant (R)-epoxide by benzylamine, followed by phosphonate ester hydrolysis and hydrogenolysis, affords the protozoal plasma membrane component (R)-2-amino-1-hydroxyethylphosphonic acid.

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