A new and expedient diastereoselective synthesis of α-(hydroxyamino)phosphonates and α-aminophosphonates by silyl triflate promoted diethyl phosphite addition to chiral N-benzyl nitrones

被引：34

作者：

De Risi, C

Perrone, D

Dondoni, A

Pollini, GP

Bertolasi, V

机构：

[1] Univ Ferrara, Dipartmento Chim, Chim Organ Lab, I-44100 Ferrara, Italy

[2] Univ Ferrara, Dipartimento Sci Farmaceut, I-44100 Ferrara, Italy

[3] Univ Ferrara, Dipartimento Chim, Ctr Strutturist Diffrattometr, I-44100 Ferrara, Italy

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2003年 / 2003卷 / 10期

关键词：

asymmetric synthesis; enzyme inhibitors; nitrones; peptidomimetics; phosphonates;

D O I：

10.1002/ejoc.200200698

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient methodology for the synthesis of alpha-aminophosphonates has been developed taking advantage of the tertbutyldimethylsilyl triflate activated addition of diethyl phosphite to N-benzyl nitrones; derived from chiral alpha-alkoxy and alpha-(Boc-amino) aldehydes. The stereoselective carbon-phosphorus bond-forming reaction proceeded smoothly to give a-(hydroxyamino)phosphonate intermediates as the primary adducts, which were subsequently converted into the corresponding polyhydroxylated alpha-amino- and alpha,beta-diaminophosphonates by conventional reductive processes. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003).

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页码：1904 / 1914

页数：11

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