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)

Full Text: HTML

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.


Related Compounds

Related Articles:

SnAP reagents for the transformation of aldehydes into substituted thiomorpholines--an alternative to cross-coupling with saturated heterocycles.

2013-02-04

[Angew. Chem. Int. Ed. Engl. 52(6) , 1705-8, (2013)]

SnAP reagents for the one-step synthesis of medium-ring saturated N-heterocycles from aldehydes.

2014-04-01

[Nature Chemistry 6(4) , 310-4, (2014)]

One-step synthesis of saturated spirocyclic N-heterocycles with stannyl amine protocol (SnAP) reagents and ketones.

2014-12-24

[J. Am. Chem. Soc. 136(51) , 17726-9, (2014)]

More Articles...