PREPARATION AND REGIOSELECTIVE AND DIASTEREOSELECTIVE REACTIONS OF ALLYLIC ZIRCONIUM REAGENTS FROM ALLYLIC ETHER DERIVATIVES

被引:77
作者
ITO, H [1 ]
TAGUCHI, T [1 ]
HANZAWA, Y [1 ]
机构
[1] TOKYO COLL PHARM,1432-1 HORINOUCHI,HACHIOJI,TOKYO 19203,JAPAN
关键词
ZIRCONOCENE; ZIRCONACYCLES; ALLYLIC ETHER DERIVATIVES; ALLYLIC ZIRCONIUM REAGENT; HOMOALLYLIC ALCOHOL DERIVATIVES;
D O I
10.1016/S0040-4039(00)91605-8
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Allylic zirconium reagents were generated by treating allylic ether derivatives with zirconocene ''Cp2Zr''. The allylic zirconium reagents reacted with aldehydes in highly regio- and diastereoselective manner to give homoallylic alcohol compounds.
引用
收藏
页码:1295 / 1298
页数:4
相关论文
共 19 条
[1]   GROUP-4 METAL-COMPLEXES OF BENZYNES, CYCLOALKYNES, ACYCLIC ALKYNES, AND ALKENES [J].
BUCHWALD, SL ;
NIELSEN, RB .
CHEMICAL REVIEWS, 1988, 88 (07) :1047-1058
[2]   SYNTHESIS, STRUCTURE, AND REACTIONS OF (1-ETHOXYETHYL)ZIRCONOCENE CHLORIDE, A STABLE ACYCLIC SECONDARY ZIRCONOCENE ALKYL [J].
BUCHWALD, SL ;
NIELSEN, RB ;
DEWAN, JC .
ORGANOMETALLICS, 1988, 7 (11) :2324-2328
[3]  
BUCHWALD SL, 1989, CHEM SCRIPTA, V29, P417
[4]   THE STEREOCHEMICAL ASSIGNMENT OF THE 1,2-DIPHENYLBUT-3-EN-1-OLS, (1RS,2RS,3RS)-3,4-EPOXY-1,2-DIPHENYLBUTAN-1-OL AND (1RS,2RS,3SR)-3,4-EPOXY-1,2-DIPHENYLBUTAN-1-OL AND (2RS,3SR)-3,4-EPOXY-1,2-DIPHENYLBUTAN-1-ONE AND (2RS,3RS)-3,4-EPOXY-1,2-DIPHENYLBUTAN-1-ONE AND CRYSTAL-STRUCTURE OF (1RS,2RS,3RS)-3,4-EPOXY-1,2-DIPHENYLBUTAN-1-OL-O [J].
COXON, JM ;
SIMPSON, GW ;
STEEL, PJ ;
TRENERRY, VC .
AUSTRALIAN JOURNAL OF CHEMISTRY, 1984, 37 (01) :65-72
[5]  
FUJITA K, 1982, HELV CHIM ACTA, V117, P1258
[6]   DIASTEREOGENIC ADDITION OF CROTYLMETAL COMPOUNDS TO ALDEHYDES [J].
HOFFMANN, RW .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1982, 21 (08) :555-566
[7]  
Ito H., UNPUB
[8]  
KARLSSON S, 1991, J ORGANOMET CHEM, V403, P113
[9]   STRUCTURES OF MONO-(2-BUTENYL) AND BIS(2-BUTENYL)ZIRCONIUM COMPLEXES IN SOLUTION AND THREO SELECTIVE INSERTION REACTION OF ALIPHATIC-ALDEHYDES [J].
MASHIMA, K ;
YASUDA, H ;
ASAMI, K ;
NAKAMURA, A .
CHEMISTRY LETTERS, 1983, (02) :219-222
[10]   METAL-PROMOTED CYCLIZATION .11. REACTION OF ZIRCONOCENE DICHLORIDE WITH ALKYLLITHIUMS OR ALKYL GRIGNARD-REAGENTS AS A CONVENIENT METHOD FOR GENERATING A ZIRCONOCENE EQUIVALANT AND ITS USE IN ZIRCONIUM-PROMOTED CYCLIZATION OF ALKENES, ALKYNES, DIENES, ENYNES, AND DIYNES [J].
NEGISHI, E ;
CEDERBAUM, FE ;
TAKAHASHI, T .
TETRAHEDRON LETTERS, 1986, 27 (25) :2829-2832