Investigation of the Configurational Stabilities of Chiral Isocyanoacetates in Multicomponent Reactions

详细信息    查看全文

• 作者：Daniel W. Carney ; Jonathan V. Truong ; Jason K. Sello
• 刊名：Journal of Organic Chemistry
• 出版年：2011
• 出版时间：December 16, 2011
• 年：2011
• 卷：76
• 期：24
• 页码：10279-10285
• 全文大小：307K
• 年卷期：v.76,no.24(December 16, 2011)
• ISSN：1520-6904

文摘

Isocyanoacetates are uniquely reactive compounds characterized by an ambivalent isocyano functional group and an enolizable 伪-carbon. It is widely believed that chiral 伪-substituted isocyanoacetates are configurationally unstable in some synthetically useful isocyanide-based multicomponent reactions. Herein, we demonstrate that chiral isocyanoacetates can be used with minimal to negligible epimerization in a variety of canonical Ugi four-component condensations as well as Joulli茅鈥揢gi three-component condensations, reactions that are particularly useful for constructing complex peptide structures in a single synthetic operation.