Are β-acylaminoacrylates hydrogenated in the same way as α-acylaminoacrylates?

被引：39

作者：

Drexler, HJ

Baumann, W

Schmidt, T

Zhang, SL

Sun, AL

Spannenberg, A

Fischer, C

Buschmann, H

Heller, D

机构：

[1] Univ Rostock eV, Leibniz Inst Organ Katalyse, D-18055 Rostock, Germany

[2] Henan Normal Univ Xinxiang, Coll Chem & Environm Sci, Henan 453007, Peoples R China

[3] ESTEVE, Barcelona 08041, Spain

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2005年 / 44卷 / 08期

关键词：

asymmetric catalysis; beta-amino acids; catalyst-substrate complexes; hydrogenation; reaction mechanisms;

D O I：

10.1002/anie.200461716

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Five catalyst-substrate complexes of the type [Rh(chiral ligand)(β-dehydroamino acid derivative)]BF4 were characterized for the first time by X-ray analysis (see example). Low-temperature NMR spectroscopy proved that three of these complexes are "major" substrate complexes, which lead to the main product in asymmetric hydrogenation, contrary to the known classical examples with analogous α-dehydroamino acid derivatives. © 2005 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

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页码：1184 / 1188

页数：5

相关论文

共 39 条

[21] Mechanism of asymmetric hydrogenation of α-(acylamino)acrylic esters catalyzed by BINAP-ruthenium(II) diacetate [J].

Kitamura, M ;

Tsukamoto, M ;

Bessho, Y ;

Yoshimura, M ;

Kobs, U ;

Widhalm, M ;

Noyori, R .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (23) :6649-6667

[22]

Landis C. R., 2000, Angew. Chem, V112, P2985

[23]

Landis CR, 2000, ANGEW CHEM INT EDIT, V39, P2863, DOI 10.1002/1521-3773(20000818)39:16<2863::AID-ANIE2863>3.0.CO

[24]

2-K

[25] ASYMMETRIC HYDROGENATION OF METHYL-(Z)-ALPHA-ACETAMIDOCINNAMATE CATALYZED BY (1,2-BIS((PHENYL-ORTHO-ANISOYL)PHOSPHINO)ETHANE)RHODIUM(I) - KINETICS, MECHANISM, AND ORIGIN OF ENANTIOSELECTION [J].

LANDIS, CR ;

HALPERN, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (06) :1746-1754

[26] ENANTIOSELECTIVE SYNTHESIS OF BETA-AMINO ACIDS BASED ON BINAP - RUTHENIUM(II) CATALYZED HYDROGENATION [J].

LUBELL, WD ;

KITAMURA, M ;

NOYORI, R .

TETRAHEDRON-ASYMMETRY, 1991, 2 (07) :543-554

[27]

Ma J. A., 2003, ANGEW CHEM, V115, P4426

[28] Recent developments in the catalytic asymmetric synthesis of α- and β-amino acids [J].

Ma, JA .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (36) :4290-4299

[29] CATALYST SUBSTRATE ADDUCTS IN ASYMMETRIC CATALYTIC-HYDROGENATION - CRYSTAL AND MOLECULAR-STRUCTURE OF [((R,R)-1,2-BIS(PHENYL-ORTHO-ANISOYLPHOSPHINO)ETHANE)(METHYL (Z)-BETA-PROPYL-ALPHA-ACETAMIDOACRYLATE)]RHODIUM TETRAFLUOROBORATE, [RH(DIPAMP)(MPAA)]BF4 [J].

MCCULLOCH, B ;

HALPERN, J ;

THOMPSON, MR ;

LANDIS, CR .

ORGANOMETALLICS, 1990, 9 (05) :1392-1395

[30] 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

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