利用环己二烯酮的不对称去对称化分子内施陶丁格反应对氢化苯并呋喃酮进行对映选择性合成。
Enantioselective Synthesis of Hydrobenzofuranones Using an Asymmetric Desymmetrizing Intramolecular Stetter Reaction of Cyclohexadienones.
作者信息
Liu Qin, Rovis Tomislav
机构信息
Department of Chemistry, Colorado State University, Fort Collins, Colorado 80523, USA.
出版信息
Org Process Res Dev. 2007;11(3):598-604. doi: 10.1021/op600278f.
Abstract
A series of cyclohexadienones were synthesized by dearomatization of phenols followed by Dess-Martin oxidation. Asymmetric intramolecular Stetter reactions of these substrates provide hydrobenzofuranones in good to excellent yields and excellent stereoselectivities. Up to three stereocenters as well as quaternary stereocenter are formed from polysubstituted substrates. A scale up experiment demonstrates the utility of this transformation.
摘要
通过酚的去芳构化反应，随后进行戴斯-马丁氧化反应，合成了一系列环己二烯酮。这些底物的不对称分子内施陶丁格反应能以良好至优异的产率和出色的立体选择性提供氢化苯并呋喃酮。多取代底物可形成多达三个立体中心以及季碳立体中心。放大实验证明了这种转化反应的实用性。
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