Diastereoselective synthesis of β-amino-α-hydroxy phosphonates via oxazaborolidine catalyzed reduction of β-phthalimido-α-keto phosphonates

被引：29

作者：

Barco, A

Benetti, S

Bergamini, P

De Risi, C

Marchetti, P

Pollini, GP

Zanirato, V

机构：

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

[2] Univ Ferrara, Dipartmento Chim, I-44100 Ferrara, Italy

[3] Ist Chim Organ, I-53100 Siena, Italy

来源：

TETRAHEDRON LETTERS | 1999年 / 40卷 / 43期

关键词：

amino acids; amino acid derivatives; Arbuzov reaction; phosphonic acids; phosphonic acid derivatives;

D O I：

10.1016/S0040-4039(99)01573-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Reduction of beta-phthalimido-alpha-keto phosphonates, obtained through an Arbuzov reaction between the appropriate acid chloride and triethyl phosphite, with boranes and oxazaborolidine as catalyst, afforded beta-phthalimido-a-hydroxy phosphonates in good yields and high diastereoselectivity. Deprotection of the amino group gave the title compounds. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：7705 / 7708

页数：4

共 10 条

[1] 4-Isopropyl-2-oxazoein-5-one anion as masked umpoled synthon for both formyl and hydroxycarbonyl anions: Generation, reactivity and synthetic applications [J].