N-Heteroarylation of Chiral 伪-Aminoesters by Means of Palladium-Catalyzed Buchwald鈥揌artwig Reaction

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• 作者：Hassan Hammoud ; Martine Schmitt ; Emilie Blaise ; Fr茅d茅ric Bihel ; Jean-Jacques Bourguignon
• 刊名：The Journal of Organic Chemistry
• 出版年：2013
• 出版时间：August 16, 2013
• 年：2013
• 卷：78
• 期：16
• 页码：7930-7937
• 全文大小：400K
• 年卷期：v.78,no.16(August 16, 2013)
• ISSN：1520-6904

文摘

N-Heteroaryl-伪-amino acid derivatives are valuable pharmacological agents as peptidomimetics. Classical S_NAr methods using acid catalysis and elevated temperatures could not be extended to various 伪-amino acids and fairly electrophilic heterocyclic partners. Here, we report a mild and versatile method of N-heteroarylation of chiral 伪-aminoesters without racemization, involving Buchwald鈥揌artwig conditions. It could be extended to various 伪-amino acids and azines. This efficient N-heteroarylation leads to (i) a chemical library of putative peptidomimetics combining diverse azaheterocycles with the chiral 伪-aminoesters and their corresponding derivatives (amides, alcohols, etc.) and (ii) arginine derivatives designed as NPFF receptor ligands.