Highly Efficient RhI-Catalyzed Asymmetric Hydrogenation of β-Amino Acrylonitriles

被引：20

作者：

Ma, Miaofeng ^{[1
,2
,3
]}

Hou, Guohua ^{[2
,3
]}

Sun, Tian ^{[2
,3
]}

Zhang, Xiaowei ^{[2
,3
]}

Li, Wei ^{[2
,3
]}

Wang, Junru ^{[1
]}

Zhang, Xumu ^{[2
,3
]}

机构：

[1] NW A&F Univ, Coll Sci, Yangling 712100, Shaanxi, Peoples R China

[2] Rutgers State Univ, Dept Chem & Chem Biol, Piscataway, NJ 08854 USA

[3] Rutgers State Univ, Dept Pharmaceut Chem, Piscataway, NJ 08854 USA

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2010年 / 16卷 / 18期

基金：

美国国家卫生研究院;

关键词：

acrylonitriles; enantioselectivity; hydrogenation; P ligands; rhodium; ALPHA; BETA-UNSATURATED NITRILES; ENANTIOSELECTIVE HYDROGENATION; STEREOSELECTIVE-SYNTHESIS; COOPERATIVE CATALYSIS; ACIDS; AZIRIDINES; BASE; CYANOMETHYLATION; COMPLEX; IMINES;

D O I：

10.1002/chem.201000325

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(Figure Presented) It takes two to TangPhos: β-Amino acrylonitriles can be readily prepared from acetonitriles. Both of the E/Z isomers undergo hydrogenation with excellent enantioselectivity by using the Rh-TangPhos (TangPhos = l, 1'-ditert-butyl-(2, 2')-diphospholane) catalyst system. The products, chiral β-amino nitriles, are valuable chiral building blocks for many drugs. © 2010 Wiley-VCH Verlag GmbH&Co. KGaA.

引用

页码：5301 / 5304

页数：4

共 45 条

[1] Albert J. S., 2007, US Patent, Patent No. 035157
[2] [Anonymous], 1999, COMPREHENSIVE ASYMME
[3] Stereoselective Pincer-Complex Catalyzed C-H Functionalization of Benzyl Nitriles under Mild Conditions. An Efficient Route to β-Aminonitriles
Aydin, Juhanes
Conrad, Cathrin S.
Szabo, Kalman J.
[J]. ORGANIC LETTERS, 2008, 10 (22) : 5175 - 5178
[4] Do aziridines require Lewis acids for cleavage with ionic nucleophiles?
Bisai, A
Pandey, G
Pandey, MK
Singh, VK
[J]. TETRAHEDRON LETTERS, 2003, 44 (31) : 5839 - 5841
[5] An enantioselective synthesis of (S)-(+)-3-aminomethyl-5-methylhexanoic acid via asymmetric hydrogenation
Burk, MJ
de Koning, PD
Grote, TM
Hoekstra, MS
Hoge, G
Jennings, RA
Kissel, WS
Le, TV
Lennon, IC
Mulhern, TA
Ramsden, JA
Wade, RA
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (14) : 5731 - 5734
[6] AMINO ACID AND PEPTIDE CHEMISTRY .3. SYNTHESIS OF ENANTIOPURE N-PROTECTED AND C-PROTECTED HOMO-BETA-AMINO ACIDS BY DIRECT HOMOLOGATION OF ALPHA-AMINO-ACIDS
CAPUTO, R
CASSANO, E
LONGOBARDO, L
PALUMBO, G
[J]. TETRAHEDRON, 1995, 51 (45) : 12337 - 12350
[7] Stereoselective synthesis of 2,4,5-trisubstituted piperidines by carbonyl ene and Prins cyclisations
Cariou, CAM
Snaith, JS
[J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2006, 4 (01) : 51 - 53
[8] HOMOGENEOUS AND HETEROGENEOUS HYDROGENATION OF NITRILES IN A LIQUID-PHASE - CHEMICAL, MECHANISTIC, AND CATALYTIC ASPECTS
DEBELLEFON, C
FOUILLOUX, P
[J]. CATALYSIS REVIEWS-SCIENCE AND ENGINEERING, 1994, 36 (03): : 459 - 506
[9] Ni(II) complexes containing chiral tridentate phosphines as new catalysts for the hydroamination of activated olefins
Fadini, L
Togni, A
[J]. CHEMICAL COMMUNICATIONS, 2003, (01) : 30 - 31
[10] Asymmetric hydroamination of acrylonitrile derivatives catalyzed by Ni(II)-complexes
Fadini, Luca
Togni, Antonio
[J]. TETRAHEDRON-ASYMMETRY, 2008, 19 (22) : 2555 - 2562

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