Enantio- and Diastereoselective Synthesis of Piperidines by Coupling of Four Components in a “One-Pot” Sequence Involving Diphenylprolinol Silyl Ether Mediated Michael Reaction

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• 作者：Tatsuya Urushima ; Daisuke Sakamoto ; Hayato Ishikawa ; Yujiro Hayashi
• 刊名：Organic Letters
• 出版年：2010
• 出版时间：October 15, 2010
• 年：2010
• 卷：12
• 期：20
• 页码：4588-4591
• 全文大小：211K
• 年卷期：v.12,no.20(October 15, 2010)
• ISSN：1523-7052

文摘

An efficient, asymmetric, four-component, one-pot synthesis of highly substituted piperidines with excellent diastereo- and enantioselectivity was established through the diphenylprolinol silyl ether mediated Michael reaction of aldehyde and nitroalkene, followed by the domino aza-Henry reaction/hemiaminalization reaction and a Lewis acid mediated allylation or cyanation reaction. All carbons of the piperidine ring are substituted with different groups, and its five contiguous stereocenters are completely controlled in both relative and absolute senses.