LEWIS-ACID PROMOTED ENE-LIKE REACTIONS OF ENOL ETHERS WITH ALDEHYDES

被引:17
作者
SHODA, H [1 ]
NAKAMURA, T [1 ]
TANINO, K [1 ]
KUWAJIMA, I [1 ]
机构
[1] TOKYO INST TECHNOL,DEPT CHEM,TOKYO 152,JAPAN
关键词
D O I
10.1016/S0040-4039(00)73732-4
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Use of organoaluminum reagents induces ene-like reactions of enol silyl ethers with aldehydes, and enols having bulky silyl groups selectively afforded syn adducts.
引用
收藏
页码:6281 / 6284
页数:4
相关论文
共 20 条
[1]   YB(FOD)3-PROMOTED ENE REACTION OF ALDEHYDES WITH VINYL ETHERS [J].
DEATON, MV ;
CIUFOLINI, MA .
TETRAHEDRON LETTERS, 1993, 34 (15) :2409-2412
[2]   STEREOSELECTIVE ALDOL CONDENSATIONS VIA BORON ENOLATES [J].
EVANS, DA ;
NELSON, JV ;
VOGEL, E ;
TABER, TR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (11) :3099-3111
[3]   REINVESTIGATION OF THE DIASTEREOSELECTIVITY OF KINETIC ALDOL CONDENSATION OF CYCLOHEXANONE LITHIUM ENOLATE WITH BENZALDEHYDE [J].
HIRAMA, M ;
NODA, T ;
TAKEISHI, S ;
ITO, S .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1988, 61 (07) :2645-2646
[4]   DOUBLE HYDROXYLATION OF ENOL SILYL ETHERS - A SINGLE-STEP SYNTHESIS OF ALPHA,ALPHA'-DIHYDROXY KETONES [J].
HORIGUCHI, Y ;
NAKAMURA, E ;
KUWAJIMA, I .
TETRAHEDRON LETTERS, 1989, 30 (25) :3323-3326
[5]   NEW TRIALKYLSILYL ENOL ETHER CHEMISTRY - REGIOSPECIFIC AND STEREOSPECIFIC SEQUENTIAL ELECTROPHILIC ADDITION [J].
MAGNUS, P ;
MUGRAGE, B .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (01) :462-464
[6]   NEW TRIALKYLSILYL ENOL ETHER CHEMISTRY - SYNTHESIS OF THE BENZOMORPHANONE CORE STRUCTURE USING A STEREOELECTRONIC CONFORMATIONAL LOCK [J].
MAGNUS, P ;
COLDHAM, I .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (02) :672-673
[7]   GENERATION OF A STABLE FORMALDEHYDE-ORGANOALUMINUM COMPLEX AND ITS SYNTHETIC UTILITY [J].
MARUOKA, K ;
CONCEPCION, AB ;
HIRAYAMA, N ;
YAMAMOTO, H .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (20) :7422-7423
[8]   DIASTEREOFACIAL SELECTIVITY OF ENOLATES [J].
MCCARTHY, PA ;
KAGEYAMA, M .
JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (21) :4681-4686
[9]   ASYMMETRIC ENE REACTIONS IN ORGANIC-SYNTHESIS [J].
MIKAMI, K ;
SHIMIZU, M .
CHEMICAL REVIEWS, 1992, 92 (05) :1021-1050
[10]  
MUKAIYAMA T, 1982, ORG REACTIONS, V28, P203