An enantioselective synthesis of (R)-2-amino-1-hydroxyethylphosphonic acidby hydrolytic kinetic resolution of (+/-)-diethyl oxiranephosphonate

Authors
Wyatt, PB Blakskjaer, P
Citation
Pb. Wyatt et P. Blakskjaer, An enantioselective synthesis of (R)-2-amino-1-hydroxyethylphosphonic acidby hydrolytic kinetic resolution of (+/-)-diethyl oxiranephosphonate, TETRAHEDR L, 40(35), 1999, pp. 6481-6483
Citations number
6
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
40
Issue
35
Year of publication
1999
Pages
6481 - 6483
Database
ISI
SICI code
0040-4039(19990827)40:35<6481:AESO(A>2.0.ZU;2-U
Abstract
(+/-)-Diethyl oxiranephosphonate undergoes efficient hydrolytic kinetic res olution by (R,R)-N,N'-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanedia minocobalt(III) acetate; opening of the resultant (R)-epoxide by benzylamin e, followed by phosphonate ester hydrolysis and hydrogenolysis, affords the protozoal plasma membrane component (R)-2-amino-1-hydroxyethylphosphonic a cid. (C) 1999 Elsevier Science Ltd. All rights reserved.