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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7 Crystal data for (±)-1-benzyl-2-methyl-6-phenyl-1,2,3,6-tetrahydropyridine: C19 H21 N, 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.
