Diels-Alder Cycloadditions of Oxacyclic Allenes and α-Pyrones

被引：1
|
作者：
Wonilowicz, Laura G. [1 ]
Mehta, Milauni M. [1 ]
Kamecke, Lisa L. [1 ]
French, Sarah A. [1 ]
Garg, Neil K. [1 ]
机构：
[1] Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA
来源：
ORGANIC LETTERS | 2024年 / 26卷 / 30期
基金：
美国国家科学基金会;
关键词：
STRAINED ALLENES; GENERATION; CYCLOHEXYNE; ARYNES; INTERMEDIATE; REACTIVITY; 2-PYRONES;
D O I：
10.1021/acs.orglett.4c02294
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Reactions of alpha-pyrones with oxacyclic allenes in Diels-Alder trappings are described. We investigate regioselectivity trends and perform competition experiments to assess the influence of structural and electronic features on relative reaction rates. We also demonstrate the stereospecific trapping of an oxacyclic allene, which proceeds in high optical yield. This study provides insight into strained cyclic allene reactivity, as well as new synthetic tools for the rapid construction of complex, heterocyclic scaffolds.
引用
收藏
页码：6465 / 6470
页数：6
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