The Regio‐ and Stereoselective Synthesis of <i>trans</i>‐2,3‐Dihydropyridine <i>N</i>‐oxides and Piperidines

Hans Andersson, Magnus Gustafsson, Dan Boström, Roger Olsson, Fredrik Almqvist

Angewandte Chemie International Edition · 2009 · 44 citations · 16 references

Concepts

Abstract

Reactivity N-Own: Pyridine N-oxides can be used for the complete regio- and stereoselective synthesis of trans-substituted piperidines. The sequential addition of Grignard reagents and aldehydes or ketones to pyridine N-oxides yields a complete regio- and stereoselective trans 2,3-addition reaction in high yields, and the substituted 2,3-dihydropyridine N-oxide can be reduced to form 2,3-trans-substituted piperidines (see scheme).

References

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