ENHANCEMENT OF DIASTEREOSELECTIVITY IN THE CLAISEN REARRANGEMENT INDUCED BY REMOTE STEREOCENTERS VIA USE OF STERICALLY DEMANDING LEWIS-ACID CATALYSTS

被引:17
作者
BOECKMAN, RK
NEEB, MJ
GAUL, MD
机构
[1] Department of Chemistry University of Rochester, Rochester
关键词
D O I
10.1016/0040-4039(94)02390-W
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Several cases of significant enhancement in the diastereoselectivity of acyclic Claisen rearrangement of cyclohexenyl allyl ethers governed principally by remote asymmetric center(s) have been observed when Lewis acid catalysts are employed rather than the usual thermal rearrangement conditions.
引用
收藏
页码:803 / 806
页数:4
相关论文
共 16 条
[1]  
BARTLETT PA, 1980, TETRAHEDRON, V36, P1
[2]   PREPARATION OF SUBSTITUTED 4-PENTENALS [J].
BRANNOCK, KC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1959, 81 (13) :3379-3383
[3]   The steric course of the Claisen rearrangement [J].
Burgstahler, Albert W. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1960, 82 (17) :4681-4685
[4]   PALLADIUM(II)-CATALYZED CLAISEN REARRANGEMENT OF 1-PHENYLETHENYL 2-PROPENYL ETHERS [J].
HAYASHI, T ;
YAMAMOTO, A ;
ITO, Y .
SYNTHETIC COMMUNICATIONS, 1989, 19 (11-12) :2109-2115
[5]   CATALYSIS OF THE COPE AND CLAISEN REARRANGEMENTS [J].
LUTZ, RP .
CHEMICAL REVIEWS, 1984, 84 (03) :205-247
[6]   UNPRECEDENTED STEREOCHEMICAL CONTROL IN THE CLAISEN REARRANGEMENT OF ALLYL VINYL ETHERS USING ORGANO-ALUMINUM REAGENTS [J].
MARUOKA, K ;
NONOSHITA, K ;
BANNO, H ;
YAMAMOTO, H .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (23) :7922-7924
[7]  
MIKAMI K, 1987, TETRAHEDRON LETT, V47, P5879
[8]  
MOSSA JS, 1985, J ORG CHEM, V508, P916
[9]   ORGANOALUMINUM-PROMOTED CLAISEN REARRANGEMENT OF ALLYL VINYL ETHERS [J].
NONOSHITA, K ;
BANNO, H ;
MARUOKA, K ;
YAMAMOTO, H .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (01) :316-322
[10]   HOMOGENEOUS CATALYSIS - TRANSITION-METAL-CATALYZED CLAISEN REARRANGEMENTS [J].
SCHENCK, TG ;
BOSNICH, B .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (07) :2058-2066