Diversity of Products in the Gold-Catalyzed Cyclization of 1-Epoxy-1-alkynylcyclopropanes by Using 1-Oxyallyl Cations

被引：26
作者：
Yang, Chun-Yao [1 ]
Lin, Min-Shiun [1 ]
Liao, Hsuan-Hung [1 ]
Liu, Rai-Shung [1 ]
机构：
[1] Natl Tsing Hua Univ, Dept Chem, Hsinchu 30043, Taiwan
来源：
CHEMISTRY-A EUROPEAN JOURNAL | 2010年 / 16卷 / 09期
关键词：
alkynes; cycloaddition; epoxides; gold; oxycyclization; DIELS-ALDER REACTIONS; INTRAMOLECULAR 4+3 CYCLOADDITIONS; INTERMOLECULAR ADDITION; OXYALLYL CATION; ALLYL CATIONS; EPOXIDES; GENERATION; ALKYNES; ACCESS; CYCLOISOMERIZATION;
D O I：
10.1002/chem.200903419
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
(Chemical Presented) A highly stereoselective AuCl3-catalyzed hydrative cyclization of 1-epoxy-1-alkynylcyclopropanes was observed for cis-epoxides. Since this cyclization produced 1-oxyallyl cations efficiently, we accomplished a two-step [4+2] annulation of epoxyalkynes with dienes and enones, to provide complex oxacyclic compounds with excellent diastereoselectivity (see scheme). © 2010 Wiley-VCH Verlag GmbH & Co. KGaA.
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收藏
页码：2696 / 2699
页数：4
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