Tandem Michael Addition鈥揜ing Transformation Reactions of 3-Hydroxyoxindoles/3-Aminooxindoles with Olefinic Azlactones: Direct Access to Structurally Diverse Spirocyclic Oxindoles

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• 作者：Bao-Dong Cui ; Jian Zuo ; Jian-Qiang Zhao ; Ming-Qiang Zhou ; Zhi-Jun Wu ; Xiao-Mei Zhang ; Wei-Cheng Yuan
• 刊名：Journal of Organic Chemistry
• 出版年：2014
• 出版时间：June 6, 2014
• 年：2014
• 卷：79
• 期：11
• 页码：5305-5314
• 全文大小：468K
• 年卷期：v.79,no.11(June 6, 2014)
• ISSN：1520-6904

文摘

An efficient method for the direct construction of two classes of spirocyclic oxindoles by the reactions of 3-hydroxyoxindoles/3-aminooxindoles and (Z)-olefinic azlactones through a tandem Michael addition鈥搑ing transformation process has been developed. With DBU as the catalyst, a range of spiro-butyrolactoneoxindoles and spiro-butyrolactamoxindoles, containing an oxygen or a nitrogen heteroatom, respectively, in the spiro stereocenter, were smoothly obtained with good to excellent diastereoselectivities in high yields.