Organocatalytic synthesis of α-hydroxy and α-aminophosphonates

被引：98

作者：

Vahdat, Seyed Mohammad ^{[1
]}

Baharfar, Robabeh ^{[2
]}

Tajbakhsh, Mahmood ^{[2
]}

Heydari, Akbar ^{[3
]}

Baghbanian, Seyed Meysam ^{[4
]}

Haksar, Samad ^{[1
]}

机构：

[1] Islamic Azad Univ, Dept Chem, Ayatollah Amoli Branch, Amol, Iran

[2] Mazandaran Univ, Dept Chem, Babol Sar 47415, Iran

[3] Tarbiat Modares Univ, Dept Chem, Tehran, Iran

[4] Islamic Azad Univ, Dept Chem, Rasht Branch, Rasht, Iran

来源：

TETRAHEDRON LETTERS | 2008年 / 49卷 / 46期

关键词：

Organocatalyst; alpha-Hydroxy phosphonate; Solvent-free; alpha-Aminophosphonates;

D O I：

10.1016/j.tetlet.2008.08.094

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new and highly flexible procedure is described for the synthesis of alpha-amino- and alpha-hydroxy phosphonates. In the presence of a catalytic amount of oxalic acid (10 mol %), trimethyl phosphite reacts with aldehydes or imines (generated in situ from an aldehyde and an amine) to yield the corresponding coupled products in good yield. (C) 2008 Elsevier Ltd. All rights reserved.

引用

页码：6501 / 6504

页数：4

共 75 条

[1] Enantioselective Mannich-type reaction catalyzed by a chiral Bronsted acid
Akiyama, T
Itoh, J
Yokota, K
Fuchibe, K
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (12) : 1566 - 1568
[2] Synthesis of α-hydroxy phosphonates using a solid supported base
Alexander, CW
Albiniak, PA
Gibson, LR
[J]. PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2000, 167 : 205 - 209
[3] SYNTHESIS AND STRUCTURE-ACTIVITY-RELATIONSHIPS OF ANTIBACTERIAL PHOSPHONOPEPTIDES INCORPORATING (1-AMINOETHYL)PHOSPHONIC ACID AND (AMINOMETHYL)PHOSPHONIC ACID
ATHERTON, FR
HASSALL, CH
LAMBERT, RW
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 1986, 29 (01) : 29 - 40
[4] Lithium perchlorate diethyl ether solution: A highly efficient media for the Abramov reaction
Azizi, N
Saidi, MR
[J]. PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2003, 178 (06) : 1255 - 1259
[5] Computer-aided analysis and design of phosphonic and phosphinic enzyme inhibitors as potential drugs and agrochemicals
Berlicki, L
Kafarski, P
[J]. CURRENT ORGANIC CHEMISTRY, 2005, 9 (18) : 1829 - 1850
[6] An extremely efficient three-component reaction of aldehydes/ketones, amines, and phosphites (Kabachnik-Fields reaction) for the synthesis of α-aminophosphonates catalyzed by magnesium perchlorate
Bhagat, Srikant
Chakraborti, Asit K.
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (04) : 1263 - 1270
[7] Amberlite-IR 120 catalyzed three-component synthesis of α-amino phosphonates in one-pot
Bhattacharya, Asish K.
Rana, Kalpeshkumar C.
[J]. TETRAHEDRON LETTERS, 2008, 49 (16) : 2598 - 2601
[8] An efficient one-pot synthesis of α-amino phosphonates catalyzed by bismuth nitrate pentahydrate
Bhattacharya, Asish K.
Kaur, Tanpreet
[J]. SYNLETT, 2007, (05) : 745 - 748
[9] Planar chiral PHANOLs as double hydrogen bonding donor organocatalysts: Synthesis and catalysis
Braddock, DC
MacGilp, ID
Perry, BG
[J]. ADVANCED SYNTHESIS & CATALYSIS, 2004, 346 (9-10) : 1117 - 1130
[10] An intramolecular organocatalytic cyclopropanation reaction
Bremeyer, N
Smith, SC
Ley, SV
Gaunt, MJ
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (20) : 2681 - 2684

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