UNUSUAL 1,2-MIGRATION IN ORGANOALUMINUM CHEMISTRY, PROMOTED BY BF3.0ET2

被引:27
作者
ALEXAKIS, A [1 ]
HANAIZI, J [1 ]
JACHIET, D [1 ]
NORMANT, JF [1 ]
TOUPET, L [1 ]
机构
[1] UNIV RENNES 1,PHYS CRISTALLINE LAB,F-35042 RENNES,FRANCE
关键词
D O I
10.1016/S0040-4039(00)88783-3
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Lithim dihydropyranyl or dihydrofuranyl triorganoaluminates react with cyclohexene oxide or benzaldehyde in the presence of BF3. OEt2, not by nucleophilic attack product 1, but by 1,2 migration of α substituent from Al to the {plus sign in right half circle}-carbon, with concomitant reaction with the electrophile on the β-carbon, giving rise to product 2. © 1990.
引用
收藏
页码:1271 / 1274
页数:4
相关论文
共 17 条
[1]   SOME ASPECTS OF THE REACTIVITY OF RCU/BF3 REAGENTS TOWARDS THE ETHER LINKAGE [J].
ALEXAKIS, A ;
MANGENEY, P ;
GHRIBI, A ;
JACHIET, D ;
NORMANT, JF .
PHILOSOPHICAL TRANSACTIONS OF THE ROYAL SOCIETY A-MATHEMATICAL PHYSICAL AND ENGINEERING SCIENCES, 1988, 326 (1592) :557-564
[2]   BORON-TRIFLUORIDE ASSISTED OPENING OF EPOXIDES BY LITHIUM ALKENYL ALUMINATE REAGENTS [J].
ALEXAKIS, A ;
JACHIET, D .
TETRAHEDRON, 1989, 45 (19) :6197-6202
[3]   BORON FLUORIDE PROMOTED OPENING OF EPOXIDES BY ORGANOCOPPER AND CUPRATE REAGENTS [J].
ALEXAKIS, A ;
JACHIET, D ;
NORMANT, JF .
TETRAHEDRON, 1986, 42 (20) :5607-5619
[4]   CYCLIC VINYL ETHER CARBANIONS .2. PREPARATION AND APPLICATIONS TO THE SYNTHESIS OF CARBONYL-COMPOUNDS [J].
BOECKMAN, RK ;
BRUZA, KJ .
TETRAHEDRON, 1981, 37 (23) :3997-4006
[5]  
CRAGG GML, 1973, ORGANOBORANES ORGANI
[6]   MECHANISM AND SYNTHETIC UTILITY OF BORON-TRIFLUORIDE ETHERATE PROMOTED ORGANO-LITHIUM ADDITIONS [J].
EIS, MJ ;
WROBEL, JE ;
GANEM, B .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (12) :3693-3694
[7]   REACTIVITY OF RCU,BF3 AND R2CULI,BF3 TOWARDS THE ETHER LINKAGE - EPOXIDES, ACETALS AND ORTHOFORMATES [J].
GHRIBI, A ;
ALEXAKIS, A ;
NORMANT, JF .
TETRAHEDRON LETTERS, 1984, 25 (29) :3075-3078
[8]   PREPARATION AND REARRANGEMENT OF ALLYLALANES [J].
HOBERG, H .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1966, 5 (05) :513-&
[9]   A STEREOSELECTIVE SYNTHESIS OF FUNCTIONALIZED ALKENYLLITHIUMS AND ALKENYL CYANOCUPRATES BY THE CU(I)-CATALYZED COUPLING OF ORGANO-LITHIUM REAGENTS WITH ALPHA-LITHIATED CYCLIC ENOL ETHERS [J].
KOCIENSKI, P ;
WADMAN, S ;
COOPER, K .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (06) :2363-2365
[10]  
Kocienski P, 1989, SYNLETT, P52