Regioselective formation of endo- and exo- cyclic enamines: Both enantiomeric products accessible by the same chiral auxiliary

Synlett

Volumn , Issue 4, 2003, Pages 493-496

  Christoffers, Jens ^a   Kreidler, Burkard ^a   Oertling, Heiko ^a   Unger, Sven ^a   Frey, Wolfgang ^a  

^a UNIVERSITY OF STUTTGART   (Germany)

Author keywords

Chiral auxiliaries; Copper; Michael additions; Regioselectivity; Stereoselectivity

Indexed keywords

COPPER; DIETHYLAMINE; ENAMINE; KETONE DERIVATIVE; SPIRO COMPOUND; VALINE; VINYL DERIVATIVE;

ALDOL REACTION; ARTICLE; CATALYSIS; CHIRALITY; ENANTIOMER; MICHAEL ADDITION; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0037239888     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-37513     Document Type: Article

References (32)

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18. +].
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24. 3: C, 66.64; H, 8.55; N, 9.14. Found: C, 66.27; H, 8.17; N, 8.96
25. 3: C, 66.65; H, 6.71, Found: C, 66.82; H, 6.73.
26. 20 +149 (c 1.36, EtOH) despite lower optical purity (86% ee), see: Felk, A.; Revial, G.; Viossat, B.; Lemoine, P.; Pfau, M. Tetrahedron: Asymmetry 1994, 5, 1459.
27. 1H NMR spectroscopy and gas chromatography.
28. Crystallographic data (excluding structure factors) for the structures reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-199252 (5a), no. CCDC-199251 (6c) and no. CCDC-199250 (8). Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [fax: +44(1223)336033 or e-mail: deposit@ccdc.cam.ac.uk].
29. The nomenclature is, of course, dependent on constitution. Configurations of structures in Scheme 2 are: -5a, (S)-5b, (R)-5c, (S)-6a, (S)-6b, and (S)-6c.
30. 14
31. For preparation of the chiral phase: Scherr, O. Dissertation; Universität Stuttgart, 1997.
32. Stefane, B.; Polanc, S. New J. Chem. 2002, 26, 28.