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Angew Chem Int Ed Engl. 2009;48(18):3288-91. doi: 10.1002/anie.200900189.

The regio- and stereoselective synthesis of trans-2,3-dihydropyridine N-oxides and piperidines.

Author information

1
Department of Chemistry, Umeå University, Petrus lestadius väg, 90187 Umeå, Sweden.

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).

PMID:
19322871
DOI:
10.1002/anie.200900189
[Indexed for MEDLINE]

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