Chiral Bronsted acid catalyzed enantioselective hydrophosphonylation of imines:: Asymmetric synthesis of α-amino phosphonates

被引：276

作者：

Akiyama, T ^{[1
]}

Morita, H ^{[1
]}

Itoh, J ^{[1
]}

Fuchibe, K ^{[1
]}

机构：

[1] Gakushuin Univ, Fac Sci, Dept Chem, Toshima Ku, Tokyo 1718588, Japan

来源：

ORGANIC LETTERS | 2005年 / 7卷 / 13期

关键词：

D O I：

10.1021/ol050695e

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A cyclic phosphoric acid derivative, derived from (R)-BINOL, was used as a chiral Bronsted acid (10 mol %) in hydrophosphonylation of aldimines with diisopropyl phosphite at room temperature. alpha-Amino phosphonates were obtained with good to high enantioselectivities.

引用

页码：2583 / 2585

页数：3

共 42 条

[11] A new and highly efficient asymmetric route to cyclic α-amino phosphonates:: The first catalytic enantioselective hydrophosphonylation of cyclic imines catalyzed by chiral heterobimetallic lanthanoid complexes [J].

Gröger, H ;

Saida, Y ;

Sasai, H ;

Yamaguchi, K ;

Martens, J ;

Shibasaki, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (13) :3089-3103

[12] Transformation of arylmethylamines into α-aminophosphonic acids via metalated phosphoramidates:: Rearrangement of partly configurationally stable N-phosphorylated α-aminocarbanions [J].

Hammerschmidt, F ;

Hanbauer, M .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (19) :6121-6131

[13] PEPTIDE-SYNTHESIS CATALYZED BY AN ANTIBODY CONTAINING A BINDING-SITE FOR VARIABLE AMINO-ACIDS [J].

HIRSCHMANN, R ;

SMITH, AB ;

TAYLOR, CM ;

BENKOVIC, PA ;

TAYLOR, SD ;

YAGER, KM ;

SPRENGELER, PA ;

BENKOVIC, SJ .

SCIENCE, 1994, 265 (5169) :234-237

[14] Asymmetric organocatalysis [J].

Houk, KN ;

List, B .

ACCOUNTS OF CHEMICAL RESEARCH, 2004, 37 (08) :487-487

[15] Hydrogen bonding: Single enantiomers from a chiral-alcohol catalyst [J].

Huang, Y ;

Unni, AK ;

Thadani, AN ;

Rawal, VH .

NATURE, 2003, 424 (6945) :146-146

[16]

Jacobsen E. N., 1999, COMPREHENSIVE ASYMME, V1- 3

[17] 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

[18] BIOLOGICAL-ACTIVITY OF AMINOPHOSPHONIC ACIDS [J].

KAFARSKI, P ;

LEJCZAK, B .

PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 1991, 63 (1-2) :193-215

[19] Catalytic asymmetric synthesis of α-amino phosphonates using enantioselective carbon-carbon bond-forming reactions [J].

Kobayashi, S ;

Kiyohara, H ;

Nakamura, Y ;

Matsubara, R .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (21) :6558-6559

[20] Asymmetric synthesis of organophosphorus compounds [J].

Kolodiazhnyi, OI .

TETRAHEDRON-ASYMMETRY, 1998, 9 (08) :1279-1332

← 1 2 3 4 5 →