General asymmetric hydrogenation of hetero-aromatic ketones

被引:163
作者
Ohkuma, T
Koizumi, M
Yoshida, M
Noyori, R [1 ]
机构
[1] Nagoya Univ, Dept Chem, Chikusa Ku, Nagoya, Aichi 4648602, Japan
[2] Nagoya Univ, Res Ctr Mat Sci, Chikusa Ku, Nagoya, Aichi 4648602, Japan
关键词
D O I
10.1021/ol0000814
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] trans-RuCL2[(R)-xylbinap][(R)-daipen] or the S,S complex acts as an efficient catalyst for asymmetric hydrogenation of hetero-aromatic ketones. The hydrogenation proceeds with a substrate-to-catalyst molar ratio of 1000-40000 to give chiral alcohols in high ee and high yield. The enantioselectivity appears to be little affected by the properties of the hetero-aromatic ring. This method allows for asymmetric synthesis of duloxetine, an inhibitor of serotonin and norepinephrine uptake carriers.
引用
收藏
页码:1749 / 1751
页数:3
相关论文
共 43 条
[1]   Enzymatic resolution of (R)- and (S)-2-(1-hydroxyalkyl)thiazoles, synthetic equivalents of (R)- and (S)-2-hydroxy aldehydes [J].
Allevi, P ;
Ciuffreda, P ;
Tarocco, G ;
Anastasia, M .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (12) :4144-4147
[2]  
ASTLEFORD BA, 1997, CHIRALITY IND, V2, pCH6
[3]   OPTICALLY-ACTIVE BIPYRIDINES IN ASYMMETRIC CATALYSIS [J].
BOLM, C ;
ZEHNDER, M ;
BUR, D .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1990, 29 (02) :205-207
[4]   Ru-BICP-catalyzed asymmetric hydrogenation of aromatic ketones [J].
Cao, P ;
Zhang, XM .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (06) :2127-2129
[5]   Chiral synthesis via organoboranes.: 46.: An efficient preparation of chiral pyridino- and thiopheno-18-crown-6 ligands from enantiomerically pure C2-symmetric pyridine- and thiophenediols [J].
Chen, GM ;
Brown, HC ;
Ramachandran, PV .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (03) :721-725
[6]  
Corey EJ, 1998, ANGEW CHEM INT EDIT, V37, P1987, DOI 10.1002/(SICI)1521-3773(19980817)37:15<1986::AID-ANIE1986>3.0.CO
[7]  
2-Z
[8]   Total synthesis of dysidiolide [J].
Corey, EJ ;
Roberts, BE .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (51) :12425-12431
[9]   ASYMMETRIC-SYNTHESIS AND ABSOLUTE STEREOCHEMISTRY OF LY248686 [J].
DEETER, J ;
FRAZIER, J ;
STATEN, G ;
STASZAK, M ;
WEIGEL, L .
TETRAHEDRON LETTERS, 1990, 31 (49) :7101-7104
[10]  
Doucet H, 1998, ANGEW CHEM INT EDIT, V37, P1703, DOI 10.1002/(SICI)1521-3773(19980703)37:12<1703::AID-ANIE1703>3.0.CO