The 2-(2-Azidoethyl)cycloalkanone Strategy for Bridged Amides and Medium-Sized Cyclic Amine Derivatives in the Aube-Schmidt Reaction

作者：Macleod Fracer; Lang Stuart; Murphy John A^*

来源：Synlett, 2010, 2010(4): 529-534.

DOI：10.1055/s-0029-1219340

• Aube
• Schmidt
• rearrangement
• azide
• heterocycle
• bridged amide
• medium-ring amine
• medium-ring amide

2-(2-Azidoethyl)cycloalkanones afford bridged lactams in the Aube-Schmidt reaction, sometimes in excellent yield, and solvolysis yields derivatives of medium-ring amines. Attempts to divert the Schmidt reaction with an arene-mediated fragmentation of the normal Schmidt intermediate have led to an initial example.

• 出版日期2010-3