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氯化金（III）催化的6-氧杂-迈克尔加成反应用于非对映选择性合成稠合四氢吡喃酮

Gold (III) Chloride-Catalyzed 6-- Oxa-Michael Addition Reactions for Diastereoselective Synthesis of Fused Tetrahydropyranones.

作者信息

Ciesielski Jennifer, Lebœuf David, Stern Harry A, Frontier Alison J

机构信息

Department of Chemistry, University of Rochester, Rochester, NY 14627, USA.

出版信息

Adv Synth Catal. 2013 Jul 8;355(10):2077-2082. doi: 10.1002/adsc.201300265.

DOI:10.1002/adsc.201300265
PMID:24032002
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC3767299/
Abstract

Alkynones were treated with boron trifluoride diethyl etherate to generate β-iodoallenolates, which underwent intramolecular aldol reactions to produce cycloalkenyl alcohols. Diastereoselective oxa-Michael ring closure could then be induced by treatment with a catalytic amount of gold(III) chloride, affording highly functionalized tetrahydropyran-containing ring systems.

摘要

炔酮与三氟化硼二乙醚反应生成β-碘代烯醇盐，后者发生分子内羟醛反应生成环烯基醇。然后，用催化量的氯化金（III）处理可引发非对映选择性氧杂-迈克尔环化反应，得到高度官能化的含四氢吡喃的环系。

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本文引用的文献

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A short and flexible route to tetrahydropyran-4-ones via conjugated nitrile oxides cycloaddition and oxa-Michael cyclization: a concise diastereoselective total synthesis of (±)-diospongin A.通过共轭腈氧化物环加成和氧杂-Michael 环化反应构建四氢吡喃-4-酮的短程和灵活途径：（±）-地奥司明 A 的简洁非对映选择性全合成。
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