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DOI: 10.1055/s-2003-41434
The Aza-Silyl-Prins Reaction: A Novel Method for the Synthesis of Trans-2,6-Tetrahydropyridines
Publication History
Publication Date:
22 September 2003 (online)
Abstract
Reaction of 4-trimethylsilyl-3-butenyl-1-amines with aldehydes under mild Lewis acid conditions gives substituted tetrahydropyridines in excellent yields and with excellent trans diastereoselectivity.
Key words
Prins reaction - aldehydes - indium trichloride
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1a Silane-terminated reactions:
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1b Silicon in total synthesis:
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3a
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3b
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3c
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3d
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3e Application in total synthesis:
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Carlson R.Lundstedt T.Nordahl A.Prochazka M. Acta Chem. Scand. 1986, 522 - Leading references to recent alternative methods for the preparation of 2,6-trans substituted tetrahydropyridines:
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6a Using ring closing metathesis:
Felpin F.-X.Lebreton J. Tetrahedron Lett. 2003, 44: 527 -
6b Also see:
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6c Via a [3+2] nitrone cycloaddition reaction:
Chackalamannil S.Wang Y. Tetrahedron 1997, 53: 11203 -
6d Via organolithium/allylboration:
Bubnov YN.Klimkina EV.Ignatenko AV.Gridnev ID. Tetrahedron Lett. 1997, 38: 4631 -
6e From an ene-iminium ion cyclisation:
Agami C.Comesse S.Kadouri-Puchot C. J. Org. Chem. 2002, 67: 2424
References
Crystal data for (±)-1-benzyl-2-methyl-6-phenyl-1,2,3,6-tetrahydropyridine: C19H21N, Triclinic space group P-1, a = 7.5440 (3) Å, b = 10.0139 (4) Å, c = 11.6666 (6) Å, α = 97.125 (2)°, β = 107.223 (2)°, γ = 107.925 (2)°, Volume = 778.20 (6) Å3, Z = 2, Density (calculated) = 1.124 Mg / m3, F(000) = 284. 6346 reflections were collected, 3446 independent reflections [R 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.
8All compounds gave satisfactory analytical and spectroscopic data.