Catalytic asymmetric synthesis of α-amino phosphonates using enantioselective carbon-carbon bond-forming reactions

被引：95

作者：

Kobayashi, S ^{[1
]}

Kiyohara, H ^{[1
]}

Nakamura, Y ^{[1
]}

Matsubara, R ^{[1
]}

机构：

[1] Univ Tokyo, Grad Sch Pharmaceut Sci, Bunkyo Ku, Tokyo 1130033, Japan

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2004年 / 126卷 / 21期

关键词：

D O I：

10.1021/ja048791i

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

We have developed highly enantioselelctive reactions of silicon enolates with N-acyl-α-iminophosphonates leading to optically active α-amino phophonates. A copper (II)-diamine complex was shown to be effective in this reaction, and high levels of yield and selectivity were achieved. It is noteworthy that this reaction opens a way to various biologically important, optically active α-amino phosphonate derivatives. Copyright © 2004 American Chemical Society.

引用

页码：6558 / 6559

页数：2

共 25 条

[1] Enantioselective synthesis of α-hydroxy and α-amino phosphonates via catalytic asymmetric hydrogenation [J].

Burk, MJ ;

Stammers, TA ;

Straub, JA .

ORGANIC LETTERS, 1999, 1 (03) :387-390

[2] INHIBITORS OF KYNURENINE HYDROXYLASE AND KYNURENINASE INCREASE CEREBRAL FORMATION OF KYNURENATE AND HAVE SEDATIVE AND ANTICONVULSANT ACTIVITIES [J].

CARPENEDO, R ;

CHIARUGI, A ;

RUSSI, P ;

LOMBARDI, G ;

CARLA, V ;

PELLICCIARI, R ;

MORONI, F ;

MATTOLI, L .

NEUROSCIENCE, 1994, 61 (02) :237-244

[3] OPTICALLY-ACTIVE 1-AMINOALKYLPHOSPHONIC ACIDS [J].

DHAWAN, B ;

REDMORE, D .

PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 1987, 32 (3-4) :119-144

[4] Enantioselective and diastereoselective mukaiyama-Michael reactions catalyzed by bis(oxazoline) Copper(II) complexes [J].

Evans, DA ;

Scheidt, KA ;

Johnston, JN ;

Willis, MC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (19) :4480-4491

[5]

Gröger H, 2000, CHEM-EUR J, V6, P943

[6]

ISHIKAWA K, 1994, Patent No. 0623625

[7] Thiourea-catalyzed enantioselective hydrophosphonylation of imines:: Practical access to enantiomerically enriched α-amino phosphonic acids [J].

Joly, GD ;

Jacobsen, EN .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (13) :4102-4103

[8]

Kafarski P, 2000, AMINOPHOSPHONIC AMIN, P407

[9] A new methodology for the stereoselective synthesis of 4-substituted butenolides: Asymmetric Michael addition reaction of 2-(trimethylsilyloxy)furans to oxazolidinone enoates [J].

Kitajima, H ;

Ito, K ;

Katsuki, T .

TETRAHEDRON, 1997, 53 (50) :17015-17028

[10]

KITAMURA M, 1989, TETRAHEDRON LETT, V30, P247

← 1 2 3 →