P-Chirogenic phosphonium salts: preparation and use in Rh-catalyzed asymmetric hydrogenation of enamides

被引：25

作者：

Danjo, H ^{[1
]}

Sasaki, W ^{[1
]}

Miyazaki, T ^{[1
]}

Imamoto, T ^{[1
]}

机构：

[1] Chiba Univ, Dept Chem, Fac Sci, Inage Ku, Chiba 2638522, Japan

来源：

TETRAHEDRON LETTERS | 2003年 / 44卷 / 17期

关键词：

D O I：

10.1016/S0040-4039(03)00668-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

P-Chirogenic trialkylphosphonium salts were prepared from the corresponding free phosphines by treatment with a strong acid (HBF4 or HOPf). No racemization of the phosphonium salts occurred in methanol or water even at considerably high temperature. The salts were conveniently used in rhodium-catalyzed asymmetric hydrogenation of enamides. (C) 2003 Elsevier Science Ltd. All rights reserved.

引用

页码：3467 / 3469

页数：3

共 12 条

[1]

Gridnev ID, 2001, ADV SYNTH CATAL, V343, P118, DOI 10.1002/1615-4169(20010129)343:1<118::AID-ADSC118>3.0.CO

[2]

2-Z

[3] P-chiral bis(trialkylphosphine) ligands and their use in highly enantioselective hydrogenation reactions [J].

Imamoto, T ;

Watanabe, J ;

Wada, Y ;

Masuda, H ;

Yamada, H ;

Tsuruta, H ;

Matsukawa, S ;

Yamaguchi, K .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (07) :1635-1636

[4] Rh(I)-catalyzed enantioselective hydrogenation of (E)- and (Z)-β-(acylamino)acrylates using 1,4-bisphosphine ligands under mild conditions [J].

Lee, S ;

Zhang, YJ .

ORGANIC LETTERS, 2002, 4 (14) :2429-2431

[5]

LUCKENBACH R, 1973, DYNAMIC STEREOCHEMIS

[6] AN EFFICIENT PROCEDURE FOR THE SYNTHESIS OF C-CHIRAL BISPHOSPHINES [J].

MCKINSTRY, L ;

LIVINGHOUSE, T .

TETRAHEDRON, 1995, 51 (28) :7655-7666

[7] AN EFFICIENT PROCEDURE FOR THE SYNTHESIS OF ELECTRON-RICH BISPHOSPHINES CONTAINING HOMOCHIRAL BACKBONES [J].

MCKINSTRY, L ;

LIVINGHOUSE, T .

TETRAHEDRON LETTERS, 1994, 35 (50) :9319-9322

[8] Air-stable trialkylphosphonium salts: Simple, practical, and versatile replacements for air-sensitive trialkylphosphines. Applications in stoichiometric and catalytic processes [J].

Netherton, MR ;

Fu, GC .

ORGANIC LETTERS, 2001, 3 (26) :4295-4298

[9] Highly enantioselective rhodium-catalyzed hydrogenation of β-dehydroamino acid derivatives using monodentate phosphoramidites [J].

Peña, D ;

Minnaard, AJ ;

de Vries, JG ;

Feringa, BL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (49) :14552-14553

[10] Highly efficient synthesis of chiral β-amino acid derivatives via asymmetric hydrogenation [J].

Tang, WJ ;

Zhang, XM .

ORGANIC LETTERS, 2002, 4 (23) :4159-4161

← 1 2 →