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

被引:189
作者
Abe, H
Amii, H [1 ]
Uneyama, K
机构
[1] Okayama Univ, Fac Engn, Dept Appl Chem, Okayama 7008530, Japan
[2] Okayama Univ, Grad Sch Nat Sci & Technol, Venture Business Lab, Okayama 7008530, Japan
关键词
D O I
10.1021/ol0002471
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] Under hydrogen pressure, a catalytic amount of palladium(II) trifluoroacetate and 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (BINAP) promoted asymmetric hydrogenation of alpha -fluorinated iminoesters to afford highly enantioenriched beta -fluorinated alpha -amino esters. The yield and ee were much improved by employing fluorinated alcohols such as 2,2,2-trifluoroethanol (up to 91% eel.
引用
收藏
页码:313 / 315
页数:3
相关论文
共 53 条
[1]   Practical synthesis of chiral sultam auxiliaries: 3-substituted-1,2-benzisothiazoline 1,1-dioxides [J].
Ahn, KH ;
Ham, C ;
Kim, SK ;
Cho, CW .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (20) :7047-7048
[2]   Palladium-catalyzed tert-butoxycarbonylation of trifluoroacetimidoyl iodides [J].
Amii, H ;
Kishikawa, Y ;
Kageyama, K ;
Uneyama, K .
JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (11) :3404-3408
[3]   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
[4]   CATALYTIC ASYMMETRIC HYDROGENATION OF IMINES - USE OF RHODIUM(I)/PHOSPHINE COMPLEXES AND CHARACTERIZATION OF RHODIUM(I)/IMINE COMPLEXES [J].
BECALSKI, AG ;
CULLEN, WR ;
FRYZUK, MD ;
JAMES, BR ;
KANG, GJ ;
RETTIG, SJ .
INORGANIC CHEMISTRY, 1991, 30 (26) :5002-5008
[5]  
Blaser H.-U., 1999, COMPREHENSIVE ASYMME, P247
[6]   ENANTIOSELECTIVE TRANSITION METAL-CATALYZED HYDROGENATION FOR THE ASYMMETRIC-SYNTHESIS OF AMINES [J].
BOLM, C .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1993, 32 (02) :232-233
[7]   SYNTHESIS OF OPTICALLY PURE (R)-ALPHA-TRIFLUOROMETHYL-ALANINE AND (S)-ALPHA-TRIFLUOROMETHYL-ALANINE [J].
BRAVO, P ;
CAPELLI, S ;
MEILLE, SV ;
VIANI, F ;
ZANDA, M ;
KUKHAR, VP ;
SOLOSHONOK, VA .
TETRAHEDRON-ASYMMETRY, 1994, 5 (10) :2009-2018
[8]  
BURGER K, 1990, SYNTHESIS-STUTTGART, P115
[9]   ENANTIOSELECTIVE HYDROGENATION OF THE C=N GROUP - A CATALYTIC ASYMMETRIC REDUCTIVE AMINATION PROCEDURE [J].
BURK, MJ ;
FEASTER, JE .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (15) :6266-6267
[10]   CATALYTIC ASYMMETRIC REDUCTIVE AMINATION OF KETONES VIA HIGHLY ENANTIOSELECTIVE HYDROGENATION OF THE C=N DOUBLE-BOND [J].
BURK, MJ ;
MARTINEZ, JP ;
FEASTER, JE ;
COSFORD, N .
TETRAHEDRON, 1994, 50 (15) :4399-4428