Stereoselective catalytic Tishchenko reduction of β-hydroxyketones using scandium triflate

被引:24
作者
Gillespie, KM [1 ]
Munslow, IJ [1 ]
Scott, P [1 ]
机构
[1] Univ Warwick, Dept Chem, Coventry CV4 7AL, W Midlands, England
关键词
scandium; scandium compounds; reduction; aldols; diastereoselection;
D O I
10.1016/S0040-4039(99)01986-3
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A number of aliphatic and aromatic beta-hydroxyketones were reduced to 1,3-diol monoesters by aldehydes in the presence of a catalytic amount of scandium triflate. Chiral substrates were reduced with high 1,3-anti diastereoselectivity. (C) 1999 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:9371 / 9374
页数:4
相关论文
共 17 条
[1]   STUDIES ON ASYMMETRIC-SYNTHESIS OF BETA-HYDROXY-DELTA-LACTONE INHIBITORS OF HMGCOA REDUCTASE .1. A NEW PREPARATION OF THE LACTONE MOIETY OF COMPACTIN [J].
BONADIES, F ;
DIFABIO, R ;
GUBBIOTTI, A ;
MECOZZI, S ;
BONINI, C .
TETRAHEDRON LETTERS, 1987, 28 (06) :703-706
[2]   DIRECTED REDUCTION OF BETA-HYDROXY KETONES EMPLOYING TETRAMETHYLAMMONIUM TRIACETOXYBOROHYDRIDE [J].
EVANS, DA ;
CHAPMAN, KT ;
CARREIRA, EM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (11) :3560-3578
[3]   SAMARIUM-CATALYZED INTRAMOLECULAR TISHCHENKO REDUCTION OF BETA-HYDROXY KETONES - A STEREOSELECTIVE APPROACH TO THE SYNTHESIS OF DIFFERENTIATED ANTI 1,3-DIOL MONOESTERS [J].
EVANS, DA ;
HOVEYDA, AH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (17) :6447-6449
[4]   REDUCTION OF BETA-HYDROXY KETONES WITH CATECHOLBORANE - A STEREOSELECTIVE APPROACH TO THE SYNTHESIS OF SYN 1,3-DIOLS [J].
EVANS, DA ;
HOVEYDA, AH .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (18) :5190-5192
[5]   A FACILE ENTRY TO BETA,DELTA-DIKETO AND SYN-BETA,DELTA-DIHYDROXY ESTERS [J].
HANAMOTO, T ;
HIYAMA, T .
TETRAHEDRON LETTERS, 1988, 29 (49) :6467-6470
[6]   STEREOSELECTIVE SYNTHESES OF BUILDING-BLOCKS WITH 3 CONSECUTIVE STEREOGENIC CENTERS - IMPORTANT PRECURSORS OF POLYKETIDE NATURAL-PRODUCTS [J].
HOFFMANN, RW .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1987, 26 (06) :489-503
[7]   1,3-SYN DIASTEREOSELECTIVE REDUCTION OF BETA-HYDROXYKETONES WITH DIISOBUTYLALUMINUM HYDRIDE AND TRIBUTYLTIN HYDRIDE [J].
KIYOOKA, S ;
KURODA, H ;
SHIMASAKI, Y .
TETRAHEDRON LETTERS, 1986, 27 (26) :3009-3012
[8]  
Kobayashi S, 1999, EUR J ORG CHEM, V1999, P15
[9]   STEREOSELECTIVE REDUCTION OF BETA-ALKOXY KETONES - A SYNTHESIS OF SYN-1,3-DIOLS [J].
MORI, Y ;
KUHARA, M ;
TAKEUCHI, A ;
SUZUKI, M .
TETRAHEDRON LETTERS, 1988, 29 (42) :5419-5422
[10]   NEW CROSS-ALDOL REACTIONS - REACTIONS OF SILYL ENOL ETHERS WITH CARBONYL-COMPOUNDS ACTIVATED BY TITANIUM TETRACHLORIDE [J].
MUKAIYAMA, T ;
BANNO, K ;
NARASAKA, K .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1974, 96 (24) :7503-7509