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Categories: C-N Bond Formation > Enamines

Synthesis of α-ketoenamines

Recent Literature

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

An electrochemically intermolecular α-amination of cyclopentanone with a broad range of anilines provides various α-enaminones under metal-free conditions in very good yields in one step.
K. Hu, P. Qian, J.-H. Su, Z. Li, J. Wang, Z. Zha, Z. Wang, J. Org. Chem., 2019, 84, 1647-1653.

TBAI as catalyst and TBHP as oxidant enable a metal-free cross-coupling of enamines and electron-deficient amines through oxidative C(sp2)-N bond formation. This efficient organocatalytic synthesis of synthetically useful diaminoalkene derivatives features readily available starting materials and wide substrate scope.
Y. Yuan, W. Hou, D. Zhang-Negrerie, K. Zhaou, Y. Du, Org. Lett., 2014, 16, 5410-5113.