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Mechanistic Insights into Lewis Acid-Controlled Torquoselective Nazarov Cyclization of Activated Dienones Bearing a Chiral Sulfoxide
European Journal of Organic Chemistry ( IF 2.8 ) Pub Date : 2022-08-14 , DOI: 10.1002/ejoc.202200828
Erwann Grenet 1 , Raphaël Robidas 2 , Arie van der Lee 3 , Claude Y. Legault 4 , Xavier J. Salom-Roig 5
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Two diastereoisomeric tetrahydrocyclopentapyranones can be diastereodivergently obtained from a common activated dienone bearing a chiral sulfoxide through a Nazarov cyclization. The diastereoselectivity switch of both reactions is controlled by the nature of the Lewis acid used as promoter. Density functional theory investigations shed light on the reaction mechanism.

中文翻译:

带有手性亚砜的活化二烯酮的路易斯酸控制扭矩选择性纳扎罗夫环化的机理研究

两个非对映异构四氢环戊吡喃酮可以通过 Nazarov 环化从带有手性亚砜的常见活化二烯酮中非对映发散获得。两种反应的非对映选择性转换由用作促进剂的路易斯酸的性质控制。密度泛函理论研究揭示了反应机理。
更新日期:2022-08-14
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