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手性膦-银(I)配合物催化的具有炔酮的对映选择性中断费斯特-本纳反应:Aldol-环异构化级联反应。

Chiral Phosphine-Silver(I) Complex Catalyzed Enantioselective Interrupted Feist-Bénary Reaction with Ynones: The Aldol-Cycloisomerization Cascade.

机构信息

†Department of Chemistry, Indian Institute of Science Education and Research Bhopal, M.P. 462066, India.

‡Indian Institute of Technology Kanpur, U.P. 201086, India.

出版信息

Org Lett. 2015 Jul 2;17(13):3302-5. doi: 10.1021/acs.orglett.5b01468. Epub 2015 Jun 24.

Abstract

Silver-catalyzed interrupted Feist-Bénary reaction is described for the efficient enantioselective synthesis of dihydrofuran heterocycles. A new method has been developed for the silver(I)-(R)-BINAP complex mediated aldol-cycloisomerization cascade reaction between ynones and 1,3-diketones to provide functionalized dihydrofurans with moderate to good yields (up to 95%) and good to excellent enantiomeric excess (up to 98%). The presence of an exocyclic double bond and hydroxy group in the dihydrofuran products provides wide scope for further structural manipulation.

摘要

银催化的中断费斯特-本纳反应被描述为高效对映选择性合成二氢呋喃杂环。已经开发了一种新方法,用于银(I)-(R)-BINAP 配合物介导的炔酮和 1,3-二酮之间的醛-环异构化级联反应,以提供具有中等至良好收率(高达 95%)和良好至优秀对映体过量(高达 98%)的官能化二氢呋喃。二氢呋喃产物中环外双键和羟基的存在为进一步的结构操作提供了广泛的范围。

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