Enantiomerically pure 1,2-bis(isopropylmethylphosphino)benzene and its use in highly enantioselective Rh-catalyzed asymmetric hydrogenation

被引：38

作者：

Miura, T ^{[1
]}

Imamoto, T ^{[1
]}

机构：

[1] Chiba Univ, Grad Sch Sci & Technol, Dept Divers Sci, Inage Ku, Chiba 2638522, Japan

来源：

TETRAHEDRON LETTERS | 1999年 / 40卷 / 26期

基金：

日本学术振兴会;

关键词：

D O I：

10.1016/S0040-4039(99)00856-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new P-chiral phosphine ligand with a 1,2-phenylene unit, (S,S)-1,2-bis(isopropylmethylphosphino)benzene, has been synthesized from 1,2-bis(methylphosphino)benzene. Its rhodium complex is highly effective in asymmetric hydrogenation of dehydroamino acid methyl esters to provide enantioselectivities of up to 98%. (C) 1999 Elsevier Science Ltd. All rights reserved.

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页码：4833 / 4836

页数：4

相关论文

共 23 条

[1]

BURK MJ, 1999, HDB CHIRAL CHEM, pCH18

[2] A highly effective phosphinite ligand derived from D-mannitol for Rh-catalyzed asymmetric hydrogenation [J].

Chen, YX ;

Li, XS ;

Tong, SK ;

Choi, MCK ;

Chan, ASC .

TETRAHEDRON LETTERS, 1999, 40 (05) :957-960

[3] A NEW AND HIGHLY ENANTIOSELECTIVE SYNTHETIC ROUTE TO P-CHIRAL PHOSPHINES AND DIPHOSPHINES [J].

COREY, EJ ;

CHEN, ZL ;

TANOURY, GJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (23) :11000-11001

[4] Synthesis and application of new chiral bidentate phosphine, 2,7-di-tert-butyl-9,9-dimethyl-4,5-bis(methylphenylphosphino)xanthine [J].

Hamada, Y ;

Matsuura, F ;

Oku, M ;

Hatano, K ;

Shioiri, T .

TETRAHEDRON LETTERS, 1997, 38 (52) :8961-8964

[5] Synthesis of chiral bis(phosphinite) ligands with a tetrahydrothiophene backbone: Use in asymmetric hydrogenation [J].

Hauptman, E ;

Shapiro, R ;

Marshall, W .

ORGANOMETALLICS, 1998, 17 (23) :4976-4982

[6] Synthesis of a new class of functionalized chiral bisphospholane ligands and the application in enantioselective hydrogenations [J].

Holz, J ;

Quirmbach, M ;

Schmidt, U ;

Heller, D ;

Stürmer, R ;

Börner, A .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (22) :8031-8034

[7] A NEW P-CHIRAL BISPHOSPHINE, (S,S)-1,2-BIS(O-ETHYLPHENYL)PHENYL-PHOSPHINOETHANE, AS AN EFFECTIVE LIGAND IN CATALYTIC ASYMMETRIC HYDROGENATION OF ALPHA-(ACYLAMINO)ACRYLIC ACIDS [J].

IMAMOTO, T ;

TSURUTA, H ;

WADA, Y ;

MASUDA, H ;

YAMAGUCHI, K .

TETRAHEDRON LETTERS, 1995, 36 (45) :8271-8274

[8] SYNTHESIS AND REACTIONS OF PHOSPHINE BORANES - SYNTHESIS OF NEW BIDENTATE LIGANDS WITH HOMOCHIRAL PHOSPHINE CENTERS VIA OPTICALLY PURE PHOSPHINE BORANES [J].

IMAMOTO, T ;

OSHIKI, T ;

ONOZAWA, T ;

KUSUMOTO, T ;

SATO, K .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (13) :5244-5252

[9] 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

[10] PHOSPHINE OXIDES AND LIAIH4-NABH4-CECL3 - SYNTHESIS AND REACTIONS OF PHOSPHINE-BORANES [J].

IMAMOTO, T ;

KUSUMOTO, T ;

SUZUKI, N ;

SATO, K .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (18) :5301-5303