Organic Letters 2014-02-21

SnAP reagents for the synthesis of piperazines and morpholines.

Michael U Luescher, Cam-Van T Vo, Jeffrey W Bode

Index: Org. Lett. 16(4) , 1236-9, (2014)

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Abstract

Substituted piperazines and morpholines are valuable structural motifs in biologically active compounds, but are not easily prepared by contemporary cross-coupling approaches. In this report, we introduce SnAP reagents for the transformation of aldehydes into N-unprotected piperazines and morpholines. This approach offers simple, mild conditions compatible with aromatic, heteroaromatic, aliphatic, and glyoxylic aldehydes and provides mono- and disubstituted N-heterocycles in a single step.