Preparation of 2,3,4-trisubstituted piperidines by a formal hetero-ene reaction of amino acid derivatives

Journal of Organic Chemistry

Volumn 61, Issue 8, 1996, Pages 2829-2838

  Laschat, Sabine ^a   Fröhlich, Roland ^a   Wibbeling, Birgit ^a  

^a UNIVERSITY OF MÜNSTER   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

PIPERIDINE DERIVATIVE;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; X RAY CRYSTALLOGRAPHY;

EID: 0030014025     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo951482d     Document Type: Article

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52. Ab initio calculations by Wiberg and Murcko on 1,2-dihalo-ethanes and 1,2-haloethanols showed that the gauche conformation of X-C-C-Y systems is about 1-2 kcal/mol more stable than the antiperiplanar conformation. A similar preference for the gauche orientation of the C-C-C-O and C-C-O-C fragment contributes to the anomeric effect in 2-methoxytetrahydropyran and related systems. (a) Wiberg, K. B.; Murcko, M. A. J. Mol Struct. 1988, 163, 1. (b) Wiberg, K. B.; Murcko, M. A. J Phys. Chem. 1987, 91, 3616. (c) Wiberg, K. B.; Murcko, M. A. J. Am. Chem. Soc. 1989, 111, 4821. For a general discussion of stereoelectronic effects and the anomeric effect see: (d) Deslongchamps, P. Stereoelectronic Effects in Organic Chemistry; Pergamon Press: Oxford, 1983; p 302. (e) Graczyk, P. P.; Mikolajczyk, M. Top. Stereochem. 1994, 21, 159.
53. Ab initio calculations by Wiberg and Murcko on 1,2-dihalo-ethanes and 1,2-haloethanols showed that the gauche conformation of X-C-C-Y systems is about 1-2 kcal/mol more stable than the antiperiplanar conformation. A similar preference for the gauche orientation of the C-C-C-O and C-C-O-C fragment contributes to the anomeric effect in 2-methoxytetrahydropyran and related systems. (a) Wiberg, K. B.; Murcko, M. A. J. Mol Struct. 1988, 163, 1. (b) Wiberg, K. B.; Murcko, M. A. J Phys. Chem. 1987, 91, 3616. (c) Wiberg, K. B.; Murcko, M. A. J. Am. Chem. Soc. 1989, 111, 4821. For a general discussion of stereoelectronic effects and the anomeric effect see: (d) Deslongchamps, P. Stereoelectronic Effects in Organic Chemistry; Pergamon Press: Oxford, 1983; p 302. (e) Graczyk, P. P.; Mikolajczyk, M. Top. Stereochem. 1994, 21, 159.
54. Ab initio calculations by Wiberg and Murcko on 1,2-dihalo-ethanes and 1,2-haloethanols showed that the gauche conformation of X-C-C-Y systems is about 1-2 kcal/mol more stable than the antiperiplanar conformation. A similar preference for the gauche orientation of the C-C-C-O and C-C-O-C fragment contributes to the anomeric effect in 2-methoxytetrahydropyran and related systems. (a) Wiberg, K. B.; Murcko, M. A. J. Mol Struct. 1988, 163, 1. (b) Wiberg, K. B.; Murcko, M. A. J Phys. Chem. 1987, 91, 3616. (c) Wiberg, K. B.; Murcko, M. A. J. Am. Chem. Soc. 1989, 111, 4821. For a general discussion of stereoelectronic effects and the anomeric effect see: (d) Deslongchamps, P. Stereoelectronic Effects in Organic Chemistry; Pergamon Press: Oxford, 1983; p 302. (e) Graczyk, P. P.; Mikolajczyk, M. Top. Stereochem. 1994, 21, 159.
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58. 4 97.4/2.6) was observed as the only product. No traces of the corresponding N-benzylidene-3,3-dimethyl-6-isopropylcyclohexylamine could be detected. See also: (a) Demailly, G.; Solladie, G. Tetrahedron Lett 1977,18, 1885. (b) Demailly, G.; Solladie, G. J. Org. Chem. 1981, 46, 3102.
59. 3.
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