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The Regio‐ and Stereoselective Synthesis of trans ‐2,3‐Dihydropyridine N ‐oxides and Piperidines
Author(s) -
Andersson Hans,
Gustafsson Magnus,
Boström Dan,
Olsson Roger,
Almqvist Fredrik
Publication year - 2009
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200900189
Subject(s) - stereoselectivity , chemistry , pyridine , reagent , reactivity (psychology) , dihydropyridine , stereochemistry , grignard reagent , pyridine n oxide , medicinal chemistry , organic chemistry , catalysis , calcium , medicine , alternative medicine , pathology
Reactivity NOwn : 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).
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