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Facile synthesis of both enantiomers of (pyrrolidin-2-yl)phosphonate from l-proline

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Title: Facile synthesis of both enantiomers of (pyrrolidin-2-yl)phosphonate from l-proline
Authors: Hirata, Shigeo / Kuriyama, Masami / Onomura, Osamu
Issue Date: Dec-2011
Publisher: Elsevier BV
Citation: Tetrahedron, 67(48), pp.9411-6416; 2011
Abstract: Diastereoselective introduction of phosphono groups into l-proline derivatives at the 5-position was achieved with suitable selection of N-protecting group. N-Benzoyl-l-prolinate preferentially gave trans-phosphorylated products, which could be easily transformed into (S)-(pyrrolidin-2-yl)phosphonates. On the other hand, N-benzyloxycarbonyl-l-prolinate reacted with phosphite to give cis-substituted products, which could be easily transformed into (R)-(pyrrolidin-2-yl)phosphonates.
Keywords: (Pyrrolidin-2-yl)phosphonate / Arbusov reaction / Diastereoselective phosphorylation / l-Proline
URI: http://hdl.handle.net/10069/26344
ISSN: 00404020
DOI: 10.1016/j.tet.2011.09.080
Rights: Copyright © 2011 Elsevier Ltd. All rights reserved.
Type: Journal Article
Text Version: author
Appears in Collections:Articles in academic journal

Citable URI : http://hdl.handle.net/10069/26344

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