化学
催化作用
药物化学
对映选择合成
Diels-Alder反应
茚
有机化学
二烯
异构化
重氮
环戊二烯
路易斯酸
环加成
作者
Michael Krebs,Sabine Laschat
出处
期刊:Arkivoc
日期:2011-11-06
卷期号:2012 (3)
标识
DOI:10.3998/ark.5550190.0013.302
摘要
This work describes the investigation of the Diels-Alder reaction of the electron-rich diene trans- 1-methoxy-3-trimethylsilyloxy-1,3-butadiene (Danishefskys diene) and the non-activated dienophiles 2-cyclopentenone and 2-methyl-2-cyclopentenone with respect to reactivity, regioselectivity and stereoselectivity. An observed double bond isomerization limits the practicability of 2-cyclopentenone as a dienophile in Diels-Alder reactions. 2-Methyl-2- cylopentenone could be converted quantitatively into one regioisomeric Diels-Alder adduct, however the stereochemical control turned out to be very demanding.
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