Efficient asymmetric hydrogenation of pyridines

Angewandte Chemie - International Edition

Volumn 43, Issue 21, 2004, Pages 2850-2852

  Glorius, Frank ^a   Spielkamp, Nick ^a   Holle, Sigrid ^a   Goddard, Richard ^a   Lehmann, Christian W ^a  

^a MAX PLANCK INSTITUT FÜR KOHLENFORSCHUNG   (Germany)

Author keywords

Asymmetric synthesis; Chiral auxiliaries; Heterogeneous catalysis; Hydrogenation; Piperidines

Indexed keywords

HYDROGENATION; NONDESTRUCTIVE EXAMINATION; SUBSTITUTION REACTIONS;

PYRIDINES; SELECTIVE CHIRALITY TRANSFER; STEREOCENTERS;

STEREOCHEMISTRY;

PYRIDINE DERIVATIVE;

ARTICLE; CATALYST; CHEMICAL REACTION; CONFORMATION; HYDROGENATION; STEREOCHEMISTRY; SUBSTITUTION REACTION; SYNTHESIS;

EID: 4344711567     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200453942     Document Type: Article

References (37)

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31. In some cases the hydrogenation can be stopped at aminal 6, e.g. in the case of 6g or 6j. An investigation of their synthetic utility is ongoing and will be reported in due course.
32. 4 (CCDC-230264), respectively.
33. The absolute stereochemistry of the products was determined unequivocally by comparison of optical rotation data with literature values (3a, 3b, 3d; N-Boc derivative of 3c), by X-ray-analysis of 3i (CCDC-230263), 6g (CCDC-230265), 6j (CCDC-230266), and 7 (CCDC-230267). CCDC 230262-230267 contain the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/conts/retrieving.html (or from the Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge CB21EZ, UK; fax: (+44)1223-336-033; or deposit@ ccdc.cam.ac.uk).
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37. Whereas the reaction with acetaldehyde can be explained as a reductive amination, the reaction with acetic anhydride is less well understood since amides seem to be tolerated under the reaction conditions (see Table 1, entry 6).