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Synlett 2003(11): 1740-1742
DOI: 10.1055/s-2003-41434
LETTER
© Georg Thieme Verlag Stuttgart · New York

The Aza-Silyl-Prins Reaction: A Novel Method for the Synthesis of Trans-2,6-Tetrahydropyridines

Adrian P. Dobbs*a, Sebastien J. J. Guesnéa, Michael B. Hursthouseb, Simon J. Colesb
a School of Chemistry, University of Exeter, Stocker Road, Exeter, EX4 4QD, UK
Fax: +44(1392)263434; e-Mail: A.Dobbs@exeter.ac.uk;
b EPSRC National Crystallography Service, University of Southampton, Highfield, Southampton. SO17 1BJ, UK
Further Information

Publication History

Received 15 May 2003
Publication Date:
22 September 2003 (online)

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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

    References

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7

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.

8

All compounds gave satisfactory analytical and spectroscopic data.