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

Angewandte Chemie - International Edition

Volumn 48, Issue 18, 2009, Pages 3288-3291

  Andersson, Hans ^b   Gustafsson, Magnus ^a   Boström, Dan ^b   Olsson, Roger ^a   Almqvist, Fredrik ^b  

^a Acadia Pharmaceuticals AB   (Sweden)

^b UMEÅ UNIVERSITY   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

DIHYDROPYRIDINES; GRIGNARD REAGENT; HIGH YIELD; N-OXIDES; SEQUENTIAL ADDITION; STEREO-SELECTIVE; STEREOSELECTIVE SYNTHESIS;

ADDITION REACTIONS; ALDEHYDES; KETONES; OXIDES; PYRIDINE; STEREOCHEMISTRY;

STEREOSELECTIVITY;

1,4-DIHYDROPYRIDINE; 2-PHENYLPIPERIDINE; DIHYDROPYRIDINE DERIVATIVE; OXIDE; PIPERIDINE DERIVATIVE;

STEREOISOMERISM; SYNTHESIS;

DIHYDROPYRIDINES; OXIDES; PIPERIDINES; STEREOISOMERISM;

EID: 70349913580     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200900189     Document Type: Article

References (22)

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18. The diasteremeric ratio (d.r.) values were determined by NMR analysis of the crude reaction mixtures. The relative configuration was determined by the crystal structure of 4 i and 4 e and NMR analysis of the crystals, which proved to be the major isomer. Compounds assigned based upon comparison to 4 i and 4e and reported as major/minor: 4a 83:17,4b 82:12,4c 89:11,4d 89:11, 4e 88:12, 4f 72:28, 4g 78:22, 4h 90:10, 4i 50:50, 4j 60:40, 41 81:19 , 4m 79:21 , 4n 81:19, 4o 81:19.
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22. Compounds 3 and 7 were also accessible using Raney Nickel in 93 and 88 % yields, respectively.