Stereocontrolled alkylation of chiral pyridinium salt toward a short enantioselective access to 2-alkyl- and 2,6-dialkyl-1,2,5,6- tetrahydropyridines

European Journal of Organic Chemistry

Volumn , Issue 8, 2000, Pages 1391-1399

  Guilloteau Bertin, Bérangère ^a   Compère, Delphine ^a   Gil, Laurent ^b   Marazano, Christian ^a   Das, Bhupesh C ^a  

^a CNRS   (France)

^b FEDERAL UNIVERSITY OF OURO PRETO   (Brazil)

Author keywords

Alkaloids; Alkylations; Asymmetric synthesis; Grignard reactions; Nitrogen heterocycles

Indexed keywords

ALKALOID DERIVATIVE; INDOLIZIDINE ALKALOID; OXAZOLIDINE DERIVATIVE; PYRIDINE DERIVATIVE; PYRIDINIUM DERIVATIVE; SOLENOPSIN A;

ALKYLATION; ARTICLE; CHEMICAL MODIFICATION; CHEMICAL REACTION; CHIRALITY; REACTION ANALYSIS; REDUCTION; STEREOCHEMISTRY;

EID: 0342699622     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1099-0690(200004)2000:8<1391::AID-EJOC1391>3.0.CO;2-D     Document Type: Article

References (19)

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2. Recent reviews: [1a] P. D. Bailey, P. A. Millwood, P. D. Smith, Chem. Commun. 1998, 633-640 [1b] A. I. Meyers, G. P. Brengel, Chem. Commun. 1997, 1-8.
3. For examples of the enantioselective synthesis of 2- and 2,6-substituted 1,2,5,6-tetrahydropyridines see: [2a] P. D. Bailey, D. J. Londesbrough, T. C. Hancox, J. D. Heffernan, A. B. Holmes, J. Chem. Soc., Chem. Commun. 1994, 2543-2544 [2b] K. Rein, M. Goicoechea-Pappas, T. V. Anklekar, G. C. Hart, G. A. Smith, R. E. Gawley, J. Am. Chem. Soc. 1989, 111, 2211-2217 [2c] C. Flann, T. C. Malone, L. E. Overman, J. Am. Chem. Soc. 1987, 109, 6097-6107 [2d] A. I. Meyers, D. A. Dickman, T. R. Bailey, J. Am. Chem. Soc. 1985, 107, 7974-7978.
4. For examples of the enantioselective synthesis of 2- and 2,6- substituted 1,2,5,6-tetrahydropyridines see: [2a] P. D. Bailey, D. J. Londesbrough, T. C. Hancox, J. D. Heffernan, A. B. Holmes, J. Chem. Soc., Chem. Commun. 1994, 2543-2544 [2b] K. Rein, M. Goicoechea-Pappas, T. V. Anklekar, G. C. Hart, G. A. Smith, R. E. Gawley, J. Am. Chem. Soc. 1989, 111, 2211-2217 [2c] C. Flann, T. C. Malone, L. E. Overman, J. Am. Chem. Soc. 1987, 109, 6097-6107 [2d] A. I. Meyers, D. A. Dickman, T. R. Bailey, J. Am. Chem. Soc. 1985, 107, 7974-7978.
5. For examples of the enantioselective synthesis of 2- and 2,6- substituted 1,2,5,6-tetrahydropyridines see: [2a] P. D. Bailey, D. J. Londesbrough, T. C. Hancox, J. D. Heffernan, A. B. Holmes, J. Chem. Soc., Chem. Commun. 1994, 2543-2544 [2b] K. Rein, M. Goicoechea-Pappas, T. V. Anklekar, G. C. Hart, G. A. Smith, R. E. Gawley, J. Am. Chem. Soc. 1989, 111, 2211-2217 [2c] C. Flann, T. C. Malone, L. E. Overman, J. Am. Chem. Soc. 1987, 109, 6097-6107 [2d] A. I. Meyers, D. A. Dickman, T. R. Bailey, J. Am. Chem. Soc. 1985, 107, 7974-7978.
6. For examples of the enantioselective synthesis of 2- and 2,6- substituted 1,2,5,6-tetrahydropyridines see: [2a] P. D. Bailey, D. J. Londesbrough, T. C. Hancox, J. D. Heffernan, A. B. Holmes, J. Chem. Soc., Chem. Commun. 1994, 2543-2544 [2b] K. Rein, M. Goicoechea-Pappas, T. V. Anklekar, G. C. Hart, G. A. Smith, R. E. Gawley, J. Am. Chem. Soc. 1989, 111, 2211-2217 [2c] C. Flann, T. C. Malone, L. E. Overman, J. Am. Chem. Soc. 1987, 109, 6097-6107 [2d] A. I. Meyers, D. A. Dickman, T. R. Bailey, J. Am. Chem. Soc. 1985, 107, 7974-7978.
7. Previous use of this strategy: Y. Génisson, C. Marazano, B. C. Das, J. Org. Chem. 1993, 58, 2052-2057.
8. Chiral isoquinolinium series: D. Barbier, C. Marazano, C. Riche, B. C. Das, P. Potier, J. Org. Chem. 1998, 63, 1767-1772.
9. For two other approaches based on the stereoselective alkylation of chiral pyridinium salts see: [5a] D. L. Comins, D. H. LaMunyon, X. Chen, J. Org. Chem. 1997, 62, 8182-8187 [5b] S. Raussou, N. Urbain, P. Mangeney, A. Alexakis, Tetrahedron Letters 1996, 37, 1599-1602 and references cited therein.
10. For two other approaches based on the stereoselective alkylation of chiral pyridinium salts see: [5a] D. L. Comins, D. H. LaMunyon, X. Chen, J. Org. Chem. 1997, 62, 8182-8187 [5b] S. Raussou, N. Urbain, P. Mangeney, A. Alexakis, Tetrahedron Letters 1996, 37, 1599-1602 and references cited therein.
11. [6a] Y. Génisson, C. Marazano, M. Mehmandoust, D. Gnecco, B. C. Das, Synlett 1992, 431-434
12. [6b] Y.-S Wong, C. Marazano, D. Gnecco, Y. Génisson, A. Chiaroni, B. C. Das, J. Org. Chem. 1997, 62, 729-733.
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15. L. Gil, B. Guilloteau-Bertin, D. Compère, C. Marazano, B. C. Das, manuscript in preparation.
16. For interesting comparisons in the piperidine series see: H. Poerwono, K. Higashiyama, T. Yamauchi, H. Kubo, S. Ohmiya, H. Takahashi, Tetrahedron 1996, 54, 13955-13970 and references cited therein.
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18. For analogous results from our laboratory and general references see: Y.-S. Wong, D. Gnecco, C. Marazano, A. Chiaroni, C. Riche, A. Billion, B. C. Das, Tetrahedron 1998, 54, 9357-9372.
19. J. Quick, Y. Khȧndelwal, P. C. Meltzer, J. S. Weinberg, J Org. Chem. 1983, 48, 5199-5203.