ACYCLIC STEREOSELECTION .54. EXTENDING THE SCOPE OF THE EVANS ASYMMETRIC ALDOL REACTION - PREPARATION OF ANTI-ALDOLS AND NON-EVANS SYN-ALDOLS

被引:227
作者
WALKER, MA [1 ]
HEATHCOCK, CH [1 ]
机构
[1] UNIV CALIF BERKELEY,DEPT CHEM,BERKELEY,CA 94720
关键词
D O I
10.1021/jo00020a006
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The Evans reagent, imide 1, reacts with aldehydes under Lewis acid catalysis to give anti or ''non-Evans'' syn aldols 5 or 6, depending on the reaction conditions. This discovery considerably amplifies the synthetic utility of these important reagents for asymmetric synthesis.
引用
收藏
页码:5747 / 5750
页数:4
相关论文
共 48 条
[1]  
ANH NT, 1986, NEW J CHEM, V10, P681
[2]   STEREOSELECTIVE ALDOL REACTIONS WITH ALPHA-UNSUBSTITUTED CHIRAL ENOLATES [J].
BRAUN, M .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1987, 26 (01) :24-37
[3]   CYCLIC NITRONATES FROM THE DIASTEREOSELECTIVE ADDITION OF 1-TRIMETHYLSILYLOXYCYCLOHEXENE TO NITROOLEFINS - STARTING MATERIALS FOR STEREOSELECTIVE HENRY REACTIONS AND 1,3-DIPOLAR CYCLOADDITIONS [J].
BROOK, MA ;
SEEBACH, D .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1987, 65 (04) :836-850
[4]   MAJOR EFFECT OF THE LEAVING GROUP IN DIALKYLBORON CHLORIDES AND TRIFLATES IN CONTROLLING THE STEREOSPECIFIC CONVERSION OF KETONES INTO EITHER (E)-ENOL OR (Z)-ENOL BORINATES [J].
BROWN, HC ;
DHAR, RK ;
BAKSHI, RK ;
PANDIARAJAN, PK ;
SINGARAM, B .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (09) :3441-3442
[5]   VERSATILE CHIRAL REAGENT FOR THE HIGHLY ENANTIOSELECTIVE SYNTHESIS OF EITHER ANTI OR SYN ESTER ALDOLS [J].
COREY, EJ ;
KIM, SS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (12) :4976-4977
[6]   ACYCLIC STEREOSELECTION .48. REVERSAL OF STEREOCHEMISTRY IN THE ALDOL REACTIONS OF A CHIRAL BORON ENOLATE [J].
DANDA, H ;
HANSEN, MM ;
HEATHCOCK, CH .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (01) :173-181
[7]   SNCL4(4-TERT-BUC6H4CHO)2 - X-RAY CRYSTAL-STRUCTURE, SOLUTION NMR, AND IMPLICATIONS FOR REACTIONS AT COMPLEXED CARBONYLS [J].
DENMARK, SE ;
HENKE, BR ;
WEBER, E .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (08) :2512-2514
[8]   STEREOCHEMISTRY OF ALLYLMETAL ALDEHYDE CONDENSATIONS .2. ALLYLSTANNANES [J].
DENMARK, SE ;
WEBER, EJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (25) :7970-7971
[9]   ON THE STEREOCHEMISTRY OF ALLYLMETAL-ALDEHYDE CONDENSATIONS [J].
DENMARK, SE ;
WEBER, EJ .
HELVETICA CHIMICA ACTA, 1983, 66 (06) :1655-1660
[10]  
DENMARK SE, 1989, TETRAHEDRON, V45, P1065