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

Abstract

2-(2-Azidoethyl)cycloalkanones afford bridged lactams in the Aubé-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.

Key words

Aubé - Schmidt - rearrangement - azide - heterocycle - bridged amide - medium-ring amine - medium-ring amide

References and Notes

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19

These compounds were isolated as single isomers. The most likely stereochemistry of alkylation of the decalone enolate would afford 70 and methanolysis would convert this into 71.