Enantioselective hydrogenation of acyclic aromatic N-aryl imines catalyzed by an iridium complex of (S,S)-1,2-bis(tert-butylmethylphosphino)ethane

被引：93

作者：

Imamoto, Tsuneo ^{[1
]}

Iwadate, Noriyuki ^{[1
]}

Yoshida, Kazuhiro ^{[1
]}

机构：

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

来源：

ORGANIC LETTERS | 2006年 / 8卷 / 11期

关键词：

D O I：

10.1021/ol060546b

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An iridium(I) complex of (S,S)-1,2-bis(tert-butylmethylphosphino)ethane with tetrakis(3,5-bis(trifluoromethyl)phenyl) borate as the counterion catalyzes the hydrogenation of acyclic aromatic N-aryl imines under 1 atm of hydrogen pressure at room temperature to give the corresponding optically active secondary amines with up to 99% ee.

引用

页码：2289 / 2292

页数：4

共 71 条

[1] Pd-catalyzed asymmetric hydrogenation of α-fluorinated iminoesters in fluorinated alcohol:: A new and catalytic enantioselective synthesis of fluoro α-amino acid derivatives [J].

Abe, H ;

Amii, H ;

Uneyama, K .

ORGANIC LETTERS, 2001, 3 (03) :313-315

[2] RHODIUM(I) SULFONATED-BDPP CATALYZED ASYMMETRIC HYDROGENATION OF IMINES IN AQUEOUS ORGANIC 2-PHASE SOLVENT SYSTEMS [J].

BAKOS, J ;

OROSZ, A ;

HEIL, B ;

LAGHMARI, M ;

LHOSTE, P ;

SINOU, D .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1991, (23) :1684-1685

[3]

Blackmond DG, 2000, CHIRALITY, V12, P442, DOI 10.1002/(SICI)1520-636X(2000)12:5/6<442::AID-CHIR25>3.0.CO

[4]

2-F

[5] Efficient enantioselective hydrogenation of arylimines using aminophosphine-oxazoline iridium catalysts [J].

Blanc, C ;

Agbossou-Niedercorn, F ;

Nowogrocki, G .

TETRAHEDRON-ASYMMETRY, 2004, 15 (14) :2159-2163

[6]

Blankenstein J, 2001, ANGEW CHEM INT EDIT, V40, P4445, DOI 10.1002/1521-3773(20011203)40:23<4445::AID-ANIE4445>3.0.CO

[7]

2-V

[8]

Blaser H.-U., 1999, COMPREHENSIVE ASYMME, P247

[9] Tunable ferrocenyl diphosphine ligands for the Ir-catalyzed enantioselective hydrogenation of N-aryl imines [J].

Blaser, HU ;

Buser, HP ;

Häusel, R ;

Jalett, HP ;

Spindler, F .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2001, 621 (1-2) :34-38

[10] New mechanistic insights into the iridium- phosphanooxazoline-catalyzed hydrogenation of unfunctionalized olefins: A DFT and kinetic study [J].

Brandt, P ;

Hedberg, C ;

Andersson, PG .

CHEMISTRY-A EUROPEAN JOURNAL, 2003, 9 (01) :339-347

← 1 2 3 4 5 6 7 8 →