1,4-Bis(arylsulfonyl)-1,2,3,4-tetrahydropyridines in synthesis. Highly regio- and stereoselective SN1′ and alkylation reactions

Synlett

Volumn , Issue 1, 1998, Pages 55-57

  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: 0002240151     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1998-1566     Document Type: Article

References (19)

1. Craig, D.; Ikin, N. J.; Mathews, N.; Smith, A. M. Tetrahedron Lett. 1995, 36, 7531-7534;
2. Craig, D.; Tierney, J. P.; Williamson, C. Tetrahedron Lett. 1997, 38, 4153-4156.
3. Allylic and tertiary sulfones may be cleaved by oxaphilic Lewis acids: Trost, B. M.; Reza Ghadiri, M. J. Am. Chem. Soc. 1986, 108, 1098-1100, and references therein.
4. Simpkins, N. S. Sulphones in Organic Synthesis; Pergamon: Oxford, 1993, pp 115-117.
5. 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.
6. 3H).
7. Berry, M. B.; Craig, D. Synlett 1992, 41-44.
8. Treatment of 3a with one equivalent of t-BuOK resulted in the high-yielding formation of 2-benzylpyridine. We are currently investigating the scope and limitations of this novel pyridine-forming reaction.
9. We thank Mr Dick Sheppard and Mr Paul Hammerton of this department for these determinations.
10. o|), 2θ ≤ 126°] and 272 parameters. The absolute chirality was determined unambiguously by use of the Flack parameter which refined to a value of 0.04(5). All computations were carried out using the SHELXTL PC program system version 5.03. Atomic coordinates, bond lengths and angles, and thermal parameters for 3a, 5b and 7a have been deposited at the Cambridge Crystallographic Data Centre.
11. For a review of electrophilic substitution reactions of allylsilanes, see: Chan, T. H.; Fleming, I. Synthesis 1979, 761-786;
12. see also: Sakurai, H.; Sasaki, K.; Hosomi, A. Tetrahedron Lett. 1981, 22, 745-748.
13. +, 342.1528).
14. Toromanoff, E. Tetrahedron 1980, 36, 2809-2931.
15. Hopman, J. C. P.; van den Berg, E.; Ollero Ollero, L.; Hiemstra, H.; Speckamp, W. N. Tetrahedron Lett. 1995, 36, 4315-4318.
16. For leading references, see: Takaya, H.; Noyori, R. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon: Oxford, 1991; Vol. 8, pp 443-444.
17. Trost, B. M.; Arndt, H. C.; Strege, P. E.; Verhoeven, T. R. Tetrahedron Lett. 1976, 3477-3478.
18. We thank Dr Christopher J. Etheridge (Imperial College) for some exploratory experiments.
19. 2,3-Dihydro-4-pyridones have emerged as versatile intermediates for the enantiocontrolled synthesis of nitrogen heterocycles. See: Comins, D. L.; Joseph, S. P.; Hong, H.; Alawar, R. S.; Foti, C. J.; Zhang, Y. M.; Chen, X. H.; La Munyon, D. H.; Guerra-Weltzien, M. Pure Appl. Chem. 1997, 69, 477-481, and references therein.