1,4-Bis(arylsulfonyl)-1,2,3,4-tetrahydropyridines in synthesis. Intramolecular alkylation reactions and stereoselective synthesis of anti-2,6-disubstituted piperidines

Synlett

Volumn , Issue 1, 1998, Pages 58-60

  Craig, Donald ^a   McCague, Raymond ^b   Potter, Gerard A ^b   Williams, Meredith R V ^a  

^a IMPERIAL COLLEGE LONDON   (United Kingdom)

^b Chiroscience Limited   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002493193     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1998-1567     Document Type: Article

References (11)

1. Craig, D.; McCague, R.; Potter, G. A.; Williams, M. R. V. Synlett, 1998, 55.
2. 13C nmr and ir spectra, and which showed low-resolution ms and either elemental combustion analysis or high-resolution ms characteristics in accord with the assigned structures.
3. For a review of ionic hydrogenation, see: Kursanov, D. N.; Parnes, Z. N.; Loim, N. M. Synthesis 1974, 633-651.
4. Trost, B. M.; Arndt, H. C.; Strege, P. E.; Verhoeven, T. R. Tetrahedron Lett. 1976, 3477-3478.
5. For other syntheses, see: Takeda, M.; Jacobson, A. E.; Kanematsu, K.; May, E. L. J. Org. Chem. 1969, 34, 4154-4157;
6. Stella, L.; Raynier, B.; Surzur, J. M. Tetrahedron 1981, 37, 2843-2854.
7. Compound 14 contains four of the five rings present in the naturally occurring indole alkaloid alstonerine. See: Peterson, A. C.; Cook, J. M. J. Org. Chem. 1995, 60, 120-129, and references cited therein.
8. Bonete, P.; Nájera, C. Tetrahedron 1995, 51, 2763-2776.
9. We speculate that under the acidic conditions used for the cyclisation reaction to form 16, the minor diastereomer undergoes epimerisation via an ionisation-recombination mechanism.
10. o|), 2θ ≤ 128°] and 296 parameters. The absolute chirality was determined unambiguously by use of the Flack parameter which refined to a value of -0.06(6). Computations were carried out using the SHELXTL PC program system version 5.03.10.
11. 3 of Ts), 2.10 (1H, br d, J 13 Hz, equatorial H-3 or equatorial H-5)