A practical asymmetric synthesis of 2,6-cis-disubstituted piperidines

Tetrahedron Asymmetry

Volumn 10, Issue 11, 1999, Pages 2225-2235

  Ciblat, Stéphane ^a   Besse, Pascale ^b   Canet, Jean Louis ^a   Troin, Yves ^a   Veschambre, Henri ^b   Gelas, Jacques ^a  

^a EA 987   (France)

^b Laboratoire de Synthese   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; METHYLAMINE; PIPERIDINE DERIVATIVE; PIPERIDONE DERIVATIVE;

ARTICLE; DIASTEREOISOMER; ENANTIOMER; PARTIAL DRUG SYNTHESIS; PRIORITY JOURNAL; STEREOCHEMISTRY;

EID: 0033522725     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(99)00226-8     Document Type: Article

References (23)

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7. For a recent monograph on asymmetric routes to substituted piperidines, see: Bailey, P. D.; Millwood, P. A.; Smith, P. D. Chem. Commun. 1998, 633-640.
8. For examples of efficient asymmetric syntheses of 2,6-dialkylpiperidines, see: (a) Katritzky, A. R.; Qiu, G.; Yang, B.; Steel, P. J. J. Org. Chem. 1998, 63, 6699-6703. (b) Amat, M.; Hidalgo, J.; Llor, N.; Bosch, J. Tetrahedron: Asymmetry 1998, 9, 2419-2422, and references cited therein. (c) Meyers, A. I.; Brengel, G. P. Chem. Commun. 1997, 1-8, and references cited therein. (d) Weymann, M.; Pfrengle, W.; Schollmeyer, D.; Kunz, H. Synthesis 1997, 1151-1160. (e) Comins, D. L.; Benjelloun, N. R. Tetrahedron Lett. 1994, 35, 829-832. (f) Grierson, D. S.; Royer, J.; Guerrier, L.; Husson, H.-P. J. Org. Chem. 1986, 51, 4475-4477. (g) Royer, J.; Husson, H.-P. J. Org. Chem. 1985, 50, 670-673. (h) Guerrier, L.; Royer, J.; Grierson, D. S.; Husson, H.-P. J. Am. Chem. Soc. 1983, 105, 7754-7755.
9. For examples of efficient asymmetric syntheses of 2,6-dialkylpiperidines, see: (a) Katritzky, A. R.; Qiu, G.; Yang, B.; Steel, P. J. J. Org. Chem. 1998, 63, 6699-6703. (b) Amat, M.; Hidalgo, J.; Llor, N.; Bosch, J. Tetrahedron: Asymmetry 1998, 9, 2419-2422, and references cited therein. (c) Meyers, A. I.; Brengel, G. P. Chem. Commun. 1997, 1-8, and references cited therein. (d) Weymann, M.; Pfrengle, W.; Schollmeyer, D.; Kunz, H. Synthesis 1997, 1151-1160. (e) Comins, D. L.; Benjelloun, N. R. Tetrahedron Lett. 1994, 35, 829-832. (f) Grierson, D. S.; Royer, J.; Guerrier, L.; Husson, H.-P. J. Org. Chem. 1986, 51, 4475-4477. (g) Royer, J.; Husson, H.-P. J. Org. Chem. 1985, 50, 670-673. (h) Guerrier, L.; Royer, J.; Grierson, D. S.; Husson, H.-P. J. Am. Chem. Soc. 1983, 105, 7754-7755.
10. For examples of efficient asymmetric syntheses of 2,6-dialkylpiperidines, see: (a) Katritzky, A. R.; Qiu, G.; Yang, B.; Steel, P. J. J. Org. Chem. 1998, 63, 6699-6703. (b) Amat, M.; Hidalgo, J.; Llor, N.; Bosch, J. Tetrahedron: Asymmetry 1998, 9, 2419-2422, and references cited therein. (c) Meyers, A. I.; Brengel, G. P. Chem. Commun. 1997, 1-8, and references cited therein. (d) Weymann, M.; Pfrengle, W.; Schollmeyer, D.; Kunz, H. Synthesis 1997, 1151-1160. (e) Comins, D. L.; Benjelloun, N. R. Tetrahedron Lett. 1994, 35, 829-832. (f) Grierson, D. S.; Royer, J.; Guerrier, L.; Husson, H.-P. J. Org. Chem. 1986, 51, 4475-4477. (g) Royer, J.; Husson, H.-P. J. Org. Chem. 1985, 50, 670-673. (h) Guerrier, L.; Royer, J.; Grierson, D. S.; Husson, H.-P. J. Am. Chem. Soc. 1983, 105, 7754-7755.
11. For examples of efficient asymmetric syntheses of 2,6-dialkylpiperidines, see: (a) Katritzky, A. R.; Qiu, G.; Yang, B.; Steel, P. J. J. Org. Chem. 1998, 63, 6699-6703. (b) Amat, M.; Hidalgo, J.; Llor, N.; Bosch, J. Tetrahedron: Asymmetry 1998, 9, 2419-2422, and references cited therein. (c) Meyers, A. I.; Brengel, G. P. Chem. Commun. 1997, 1-8, and references cited therein. (d) Weymann, M.; Pfrengle, W.; Schollmeyer, D.; Kunz, H. Synthesis 1997, 1151-1160. (e) Comins, D. L.; Benjelloun, N. R. Tetrahedron Lett. 1994, 35, 829-832. (f) Grierson, D. S.; Royer, J.; Guerrier, L.; Husson, H.-P. J. Org. Chem. 1986, 51, 4475-4477. (g) Royer, J.; Husson, H.-P. J. Org. Chem. 1985, 50, 670-673. (h) Guerrier, L.; Royer, J.; Grierson, D. S.; Husson, H.-P. J. Am. Chem. Soc. 1983, 105, 7754-7755.
12. For examples of efficient asymmetric syntheses of 2,6-dialkylpiperidines, see: (a) Katritzky, A. R.; Qiu, G.; Yang, B.; Steel, P. J. J. Org. Chem. 1998, 63, 6699-6703. (b) Amat, M.; Hidalgo, J.; Llor, N.; Bosch, J. Tetrahedron: Asymmetry 1998, 9, 2419-2422, and references cited therein. (c) Meyers, A. I.; Brengel, G. P. Chem. Commun. 1997, 1-8, and references cited therein. (d) Weymann, M.; Pfrengle, W.; Schollmeyer, D.; Kunz, H. Synthesis 1997, 1151-1160. (e) Comins, D. L.; Benjelloun, N. R. Tetrahedron Lett. 1994, 35, 829-832. (f) Grierson, D. S.; Royer, J.; Guerrier, L.; Husson, H.-P. J. Org. Chem. 1986, 51, 4475-4477. (g) Royer, J.; Husson, H.-P. J. Org. Chem. 1985, 50, 670-673. (h) Guerrier, L.; Royer, J.; Grierson, D. S.; Husson, H.-P. J. Am. Chem. Soc. 1983, 105, 7754-7755.
13. For examples of efficient asymmetric syntheses of 2,6-dialkylpiperidines, see: (a) Katritzky, A. R.; Qiu, G.; Yang, B.; Steel, P. J. J. Org. Chem. 1998, 63, 6699-6703. (b) Amat, M.; Hidalgo, J.; Llor, N.; Bosch, J. Tetrahedron: Asymmetry 1998, 9, 2419-2422, and references cited therein. (c) Meyers, A. I.; Brengel, G. P. Chem. Commun. 1997, 1-8, and references cited therein. (d) Weymann, M.; Pfrengle, W.; Schollmeyer, D.; Kunz, H. Synthesis 1997, 1151-1160. (e) Comins, D. L.; Benjelloun, N. R. Tetrahedron Lett. 1994, 35, 829-832. (f) Grierson, D. S.; Royer, J.; Guerrier, L.; Husson, H.-P. J. Org. Chem. 1986, 51, 4475-4477. (g) Royer, J.; Husson, H.-P. J. Org. Chem. 1985, 50, 670-673. (h) Guerrier, L.; Royer, J.; Grierson, D. S.; Husson, H.-P. J. Am. Chem. Soc. 1983, 105, 7754-7755.
14. For examples of efficient asymmetric syntheses of 2,6-dialkylpiperidines, see: (a) Katritzky, A. R.; Qiu, G.; Yang, B.; Steel, P. J. J. Org. Chem. 1998, 63, 6699-6703. (b) Amat, M.; Hidalgo, J.; Llor, N.; Bosch, J. Tetrahedron: Asymmetry 1998, 9, 2419-2422, and references cited therein. (c) Meyers, A. I.; Brengel, G. P. Chem. Commun. 1997, 1-8, and references cited therein. (d) Weymann, M.; Pfrengle, W.; Schollmeyer, D.; Kunz, H. Synthesis 1997, 1151-1160. (e) Comins, D. L.; Benjelloun, N. R. Tetrahedron Lett. 1994, 35, 829-832. (f) Grierson, D. S.; Royer, J.; Guerrier, L.; Husson, H.-P. J. Org. Chem. 1986, 51, 4475-4477. (g) Royer, J.; Husson, H.-P. J. Org. Chem. 1985, 50, 670-673. (h) Guerrier, L.; Royer, J.; Grierson, D. S.; Husson, H.-P. J. Am. Chem. Soc. 1983, 105, 7754-7755.
15. For examples of efficient asymmetric syntheses of 2,6-dialkylpiperidines, see: (a) Katritzky, A. R.; Qiu, G.; Yang, B.; Steel, P. J. J. Org. Chem. 1998, 63, 6699-6703. (b) Amat, M.; Hidalgo, J.; Llor, N.; Bosch, J. Tetrahedron: Asymmetry 1998, 9, 2419-2422, and references cited therein. (c) Meyers, A. I.; Brengel, G. P. Chem. Commun. 1997, 1-8, and references cited therein. (d) Weymann, M.; Pfrengle, W.; Schollmeyer, D.; Kunz, H. Synthesis 1997, 1151-1160. (e) Comins, D. L.; Benjelloun, N. R. Tetrahedron Lett. 1994, 35, 829-832. (f) Grierson, D. S.; Royer, J.; Guerrier, L.; Husson, H.-P. J. Org. Chem. 1986, 51, 4475-4477. (g) Royer, J.; Husson, H.-P. J. Org. Chem. 1985, 50, 670-673. (h) Guerrier, L.; Royer, J.; Grierson, D. S.; Husson, H.-P. J. Am. Chem. Soc. 1983, 105, 7754-7755.
16. Ripoche, I.; Canet, J.-L.; Aboab, B.; Gelas, J.; Troin, Y. J. Chem. Soc., Perkin Trans. 1 1998, 3485-3492.
17. Ripoche, I.; Canet, J.-L.; Gelas, J.; Troin, Y. Eur. J. Org. Chem. 1999, in press.
18. Wenkert, E.; Dave, K. G.; Stevens, R. V. J. Am. Chem. Soc. 1968, 90, 6177.
19. For enantioselective preparation of both enantiomers of amine 7, see preceding paper.
20. Aldehyde 8 was conveniently prepared according to: Martinelli, M. J. J. Org. Chem. 1990, 55, 5065-5073. Aldehydes 9-18 are commercially available.
21. HPLC fitted out with a Daicel Chiralcel OJ column.
22. For the protection of the ketone function as a dioxane in place of a dioxolane, see Ref. 9.
23. Augustine, R. L. In Catalytic Hydrogenation; M. Dekker Inc. Ed.: New York, 1965; p. 23.