Functionalization of α,β-unsaturated esters and ketones: A facile and highly stereoselective one-pot approach to N-protected α,β-dehydroamino acid derivatives

Dianjun Chen, Li Guo, Junying Liu, Sameer Kirtane, John F. Cannon, Guigen Li

Research output: Contribution to journalArticle

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Abstract

(Chemical Equation Presented) A new, facile, and highly stereoselective protocol toward α,β-dehydroamino acid derivatives has been developed. The one-pot synthesis was very convenient to perform by using the aminohalogenation reaction of α,β-unsaturated esters and ketones followed by treatment with specific bases. Only two [2.2.2] bicyclic organic bases were found to be effective for this transformation. Good yields (58-68%) and excellent Z-selectivity were obtained for 12 examples.

Original languageEnglish
Pages (from-to)921-924
Number of pages4
JournalOrganic Letters
Volume7
Issue number5
DOIs
StatePublished - Mar 3 2005

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