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.

引用

页码：2696 / 2699

页数：4

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