Highly Diastereoselective Michael Reactions Using 尾-Nitrocarbonyl Nucleophiles

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• 作者：Amber A. S. Gietter-Burch ; Roxana E. Mitrut ; Donald A. Watson
• 刊名：Organic Letters
• 出版年：2015
• 出版时间：November 6, 2015
• 年：2015
• 卷：17
• 期：21
• 页码：5468-5471
• 全文大小：315K
• ISSN：1523-7052

文摘

We have discovered a highly diastereoselective Michael reaction of 伪-substituted, 尾-nitrocarbonyl compounds to deliver highly functionalized stereodiads containing fully substituted nitrogen-bearing centers. Good to excellent yields and diastereoselectivities are observed. This transformation is tolerant of various types of carbonyl groups on the nucleophilic partner, as well as a range of unsaturated electrophiles. Mechanistic investigations are consistent with internal hydrogen bonding in the nitroalkane tautomer as the major factor in the control of diastereoselectivity in these transformations.