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Synthesis of Functionalized Enamines: A Facile and Efficient Protocol toward N-Protected α,β-Dehydroamino Acid Derivatives

Yun Sun, Xiaozhao Wang, Xiufang Zheng, Kang Zhao*

*Tianjin Key Laboratory for Modern Drug Delivery & High-Efficiency, School of Pharmaceutical Science and Technology, Tianjin University, Tianjin 300072, P. R. of China, Email:

Y. Sun, X. Wang, X. Zheng, K. Zhao, Synlett, 2008, 861-866.

DOI: 10.1055/s-2008-1042901

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α,β-Dehydroamino acid derivatives were synthesized in good yields from α-bromoketones or α-bromoesters and hydroxamates via a sequential procedure involving displacement of bromide by hydroxamate anion, followed by a base-induced elimination-isomerization reaction.

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Key Words

α,β-dehydroamino acid derivatives, functionalized enamines, substitution, elimination, electron-withdrawing group

ID: J60-Y2008-0850