LEWIS ACID-CATALYZED HETERO-DIELS-ALDER REACTIONS OF METHYL 2-OXO-3-ALKENOATES WITH ALKENES

被引：17
|
作者：
SERA, A
OHARA, M
YAMADA, H
EGASHIRA, E
UEDA, N
SETSUNE, J
机构：
来源：
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN | 1994年 / 67卷 / 07期
关键词：
D O I：
10.1246/bcsj.67.1912
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Lewis acid-catalyzed cycloadditions of 4-substituted methyl 2-oxo-3-butenoates and -3-pentenoates with alkenes took place with high regio- and stereoselectivities to afford substituted 6-methoxycarbonyl-3,4-dihydro-2H-pyrans in good to moderate yields. None of the ene products were produced. Similar reactions of methyl 3-phenyl-2-oxo-3-butenoate with alkenes afforded both the corresponding 3,4-dihydro-2H-pyrans and a dimeric cycloadduct of the diene component. The regio- and stereoselectivities of the present inverse-electron-demand cycloadditions indicated that the reactions proceeded through a concerted exo transition state.
引用
收藏
页码：1912 / 1917
页数：6
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