1,4-Bis(arylsulfonyl)dihydropyridines in synthesis. Enantioselective synthesis of 2,3,6-trisubstituted piperidines

Journal of Organometallic Chemistry

Volumn 624, Issue 1-2, 2001, Pages 380-382

  Carballares, Santiago ^a   Craig, Donald ^a  

^a IMPERIAL COLLEGE LONDON   (United Kingdom)

Author keywords

2,3,6 Trisubstituted piperidines; Enantioselective synthesis; Organolithium

Indexed keywords

EID: 0001282201     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0022-328X(00)00918-9     Document Type: Article

References (11)

1. J.C. Adelbrecht, D. Craig, S.Thorimbert, unpublished observations.
2. D. Craig, R. McCague, G.A. Potter, M.R.V. Williams, Synlett (1998) 55.
3. D. Craig, R. McCague, G.A. Potter, M.R.V. Williams, Synlett (1998) 58.
4. J.C. Adelbrecht, D. Craig, B.W. Dymock, S. Thorimbert, Synlett (2000) 467.
5. P. Bonete, C. Najera, Tetrahedron 51 (1995) 2763.
6. 2 (0.5M).
7. Reduction may be considered to be in the Felkin-Anh sense if the benzyl and tosylamino groups are regarded as medium and large respectively. For related work on the stereoselectivity of reduction of α-aminoketones, see: F. Benedetti, S. Miertus, S. Norbedo, A. Tossi, P. Zlatoidzky, J. Org. Chem. 62 (1997) 9348 and references therein.
8. 4.
9. We thank Professor David J. Williams and Dr Andrew J.P. White of this Department for this determination.
10. R. Noyori, H. Takaya, in: B.M. Trost (Ed.), Comprehensive Organic Synthesis, vol. 8, Pergamon, Oxford, 1991, p. 443.
11. For a review of recent synthetic work on saturated nitrogen heterocycles including piperidines, and leading references, see: A. Mitchinson, A. Nadin, J. Chem. Soc. Perkin Trans. I (2000) 2862.