Intramolecular Diels-Alder Reactions of Cyclopropenone Ketals

被引：13
|
作者：
Patel, Paresma R.
Boger, Dale L. [1 ]
机构：
[1] Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA
来源：
ORGANIC LETTERS | 2010年 / 12卷 / 15期
基金：
美国国家卫生研究院;
关键词：
DELOCALIZED SINGLET VINYLCARBENES; 3-CARBON 1,1-DIPOLES 1,3-DIPOLES; CYCLOADDITION REACTIONS; THERMAL-REACTIONS; 2-CARBON CYCLOADDITION; ACETALS;
D O I：
10.1021/ol101375a
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The first intramolecular cycloaddition reactions of cyclopropenone ketals with tethered electron-deficient, electron-rich, and neutral 1-substituted dienes are reported, constituting inverse electron demand, normal, and neutral Diels-Alder reactions, that provide exclusively the exo [4 + 2] cycloaddition products without the intervention of [1 + 2], [3 + 2], or [3 + 4] cycloadducts in reactions whose courses do not depend on the reaction conditions, the diene activating substituent, or the nature of the tethering.
引用
收藏
页码：3540 / 3543
页数：4
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