Diastereoselective Control of Intramolecular Aza-Michael Reactions Using Achiral Catalysts

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• 作者：Cheng Zhong ; Yikai Wang ; Alvin W. Hung ; Stuart L. Schreiber ; Damian W. Young
• 刊名：Organic Letters
• 出版年：2011
• 出版时间：October 21, 2011
• 年：2011
• 卷：13
• 期：20
• 页码：5556-5559
• 全文大小：813K
• 年卷期：v.13,no.20(October 21, 2011)
• ISSN：1523-7052

文摘

An intramolecular aza-Michael reaction with a Cbz carbamate and an enone is reported to result in 3,5-disubstituted nitrogen-containing heterocycles. Either cis or trans isomers were obtained selectively using chiral substrates and an achiral Pd (II) complex or strong Br酶nsted acid catalysis. A range of substrates undergoes these selective transformations. Functionalization of the resulting products yielding bicyclic heterocycles is also demonstrated.