The aza-silyl-Prins reaction: A novel method for the synthesis of trans-2,6-tetrahydropyridines

Synlett

Volumn , Issue 11, 2003, Pages 1740-1742

  Dobbs, Adrian P ^a   Guesné, Sebastien J J ^a   Hursthouse, Michael B ^b   Coles, Simon J ^b  

^a UNIVERSITY OF EXETER   (United Kingdom)

^b UNIVERSITY OF SOUTHAMPTON   (United Kingdom)

Author keywords

Aldehydes; Indium trichloride; Prins reaction

Indexed keywords

ALDEHYDE DERIVATIVE; AMINE; LEWIS ACID; PYRIDINE DERIVATIVE;

ARTICLE; CYCLIZATION; DIASTEREOISOMER; DRUG SYNTHESIS; HYDROGENATION; STEREOCHEMISTRY; TECHNIQUE; TRANS ISOMER;

EID: 0042912836     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-41434     Document Type: Article

References (17)

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11. Leading references to recent alternative methods for the preparation of 2,6-trans substituted tetrahydropyridines: (a) Using ring closing metathesis: Felpin, F.-X.; Lebreton, J. Tetrahedron Lett. 2003, 44, 527. (b) Also see: Kumareswaran, R.; Hassner, A. Tetrahedron: Asymmetry 2001, 12, 2269. (c) Via a [3+2] nitrone cycloaddition reaction: Chackalamannil, S.; Wang, Y. Tetrahedron 1997, 53, 11203. (d) Via organolithium/allylboration: Bubnov, Y. N.; Klimkina, E. V.; Ignatenko, A. V.; Gridnev, I. D. Tetrahedron Lett. 1997, 38, 4631. (e) From an ene-iminium ion cyclisation: Agami, C.; Comesse, S.; Kadouri-Puchot, C. J. Org. Chem. 2002, 67, 2424.
12. Leading references to recent alternative methods for the preparation of 2,6-trans substituted tetrahydropyridines: (a) Using ring closing metathesis: Felpin, F.-X.; Lebreton, J. Tetrahedron Lett. 2003, 44, 527. (b) Also see: Kumareswaran, R.; Hassner, A. Tetrahedron: Asymmetry 2001, 12, 2269. (c) Via a [3+2] nitrone cycloaddition reaction: Chackalamannil, S.; Wang, Y. Tetrahedron 1997, 53, 11203. (d) Via organolithium/allylboration: Bubnov, Y. N.; Klimkina, E. V.; Ignatenko, A. V.; Gridnev, I. D. Tetrahedron Lett. 1997, 38, 4631. (e) From an ene-iminium ion cyclisation: Agami, C.; Comesse, S.; Kadouri-Puchot, C. J. Org. Chem. 2002, 67, 2424.
13. Leading references to recent alternative methods for the preparation of 2,6-trans substituted tetrahydropyridines: (a) Using ring closing metathesis: Felpin, F.-X.; Lebreton, J. Tetrahedron Lett. 2003, 44, 527. (b) Also see: Kumareswaran, R.; Hassner, A. Tetrahedron: Asymmetry 2001, 12, 2269. (c) Via a [3+2] nitrone cycloaddition reaction: Chackalamannil, S.; Wang, Y. Tetrahedron 1997, 53, 11203. (d) Via organolithium/allylboration: Bubnov, Y. N.; Klimkina, E. V.; Ignatenko, A. V.; Gridnev, I. D. Tetrahedron Lett. 1997, 38, 4631. (e) From an ene-iminium ion cyclisation: Agami, C.; Comesse, S.; Kadouri-Puchot, C. J. Org. Chem. 2002, 67, 2424.
14. Leading references to recent alternative methods for the preparation of 2,6-trans substituted tetrahydropyridines: (a) Using ring closing metathesis: Felpin, F.-X.; Lebreton, J. Tetrahedron Lett. 2003, 44, 527. (b) Also see: Kumareswaran, R.; Hassner, A. Tetrahedron: Asymmetry 2001, 12, 2269. (c) Via a [3+2] nitrone cycloaddition reaction: Chackalamannil, S.; Wang, Y. Tetrahedron 1997, 53, 11203. (d) Via organolithium/allylboration: Bubnov, Y. N.; Klimkina, E. V.; Ignatenko, A. V.; Gridnev, I. D. Tetrahedron Lett. 1997, 38, 4631. (e) From an ene-iminium ion cyclisation: Agami, C.; Comesse, S.; Kadouri-Puchot, C. J. Org. Chem. 2002, 67, 2424.
15. Leading references to recent alternative methods for the preparation of 2,6-trans substituted tetrahydropyridines: (a) Using ring closing metathesis: Felpin, F.-X.; Lebreton, J. Tetrahedron Lett. 2003, 44, 527. (b) Also see: Kumareswaran, R.; Hassner, A. Tetrahedron: Asymmetry 2001, 12, 2269. (c) Via a [3+2] nitrone cycloaddition reaction: Chackalamannil, S.; Wang, Y. Tetrahedron 1997, 53, 11203. (d) Via organolithium/allylboration: Bubnov, Y. N.; Klimkina, E. V.; Ignatenko, A. V.; Gridnev, I. D. Tetrahedron Lett. 1997, 38, 4631. (e) From an ene-iminium ion cyclisation: Agami, C.; Comesse, S.; Kadouri-Puchot, C. J. Org. Chem. 2002, 67, 2424.
16. int = 0.0475], which were used in all calculations. Diffractometer: Nonius KappaCCD area detector. Structure solution: SHELXS97 and structure refinement: SHELXL97. The deposition number at the Cambridge Crystallography Data Centre, CCDC, is CCDC214999.
17. All compounds gave satisfactory analytical and spectroscopic data.