ASYMMETRIC [2+2] CYCLOADDITION OF KETENE WITH ALDEHYDES CATALYZED BY ME3AL COMPLEXES OF AXIALLY CHIRAL 1,1'-BINAPHTHALENE-2,2'-DIOL DERIVATIVES

被引:30
作者
TAMAI, Y [1 ]
SOMEYA, M [1 ]
FUKUMOTO, J [1 ]
MIYANO, S [1 ]
机构
[1] TOHOKU UNIV,FAC ENGN,DEPT BIOCHEM & ENGN,AOBA KU,SENDAI,MIYAGI 980,JAPAN
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1994年 / 12期
关键词
D O I
10.1039/p19940001549
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Asymmetric [2 + 2] cycloaddition of ketene 1 with the aldehydes 2a-f, catalysed by axially chiral Lewis acids 3a-c afforded optically active 4-substituted oxetan-2-ones 4a-f in up to 56% enantiomeric excess (e.e.); the stereoselectivity of the reaction depended on the structure of the chiral Lewis acids and of the aldehydes, the order of addition of compounds 1 and 2 and on the solvents employed.
引用
收藏
页码:1549 / 1550
页数:2
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