Enantioselective synthesis of hydrobenzofuranones using an asymmetric desymmetrizing intramolecular Stetter reaction of cyclohexadienones
Enantioselective synthesis of hydrobenzofuranones using an asymmetric desymmetrizing intramolecular Stetter reaction of cyclohexadienones
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DOI：
10.1021/op600278f
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发表时间：
2007-05-01
影响因子：
3.4
通讯作者：
Rovis, Tomislav
中科院分区：
文献类型：
--
作者：
Liu, Qin;Rovis, Tomislav
以苯酚为原料，经脱芳构化和Dess-Martin氧化反应合成了一系列环己二酮。这些底物的不对称分子内Stetter反应以很好到很好的产率和良好的立体选择性提供了氢苯并呋喃酮。由多取代基底物形成多达三个立体中心以及一个四元立体中心。一项放大实验证明了这种转变的实用性。
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 a quaternary stereocenter are formed from polysubstituted substrates. A scale-up experiment demonstrates the utility of this transformation.