Stereospecific Allylation of a Serine-derived Zinc/Copper Reagent. Synthesis of Substituted Pipecolic Acid Derivatives

Synlett

Volumn 1997, Issue 7, 1997, Pages 789-790

  Jackson, Richard F W ^a   Turner, Debra ^a   Block, Michael H ^b  

^a NEWCASTLE UNIVERSITY   (United Kingdom)

^b ASTRAZENECA   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002153281     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-5769     Document Type: Article

References (20)

1. Dunn, M.J.; Jackson, R.F.W.; Pietruszka, J.; Turner, D. J.Org. Chem. 1995, 60, 2210-2215.
2. Dunn, M.J.; Jackson, R.F.W.; Stephenson, G.R. Synlett 1992, 905-906.
3. Enders, D.v. Berg, S.; Jandeleit, B. Synlett, 1996, 18-20.
4. Enders, D.; Jandeleit, B.; Raabe, G. Angew Chem. Int. Ed. Engl., 1994, 33, 1949-1951.
5. Enders, D.; Frank, U.; Fey, P.; Jandeleit, B.; Lohray, B.B. J. Organomet. Chem. 1996, 519, 147-159.
6. 3-allyl)iron tetracarbonyl salt 7 or 9 (0.5 mmol) at -78 °C (no additional solvent). The resulting mixture was stirred under argon and the temperature was allowed to rise to -20 °C. The reaction mixture was stirred overnight at this temperature. Ceric ammonium nitrate (55 mg, 0.6 mmol) in water (0.5 mL) was then added and the reaction was stirred for six hours. The reaction mixture was filtered and partitioned between diethyl ether (25 mL) and water (25 mL). The organic extracts were washed with saturated aqueous ammonium fluoride (10 mL), saturated sodium thiosulphate (10 mL), saturated sodium chloride (25 mL), and water (3 × 25 mL). Finally, the organic extracts were dried over magnesium sulphate and concentrated under reduced pressure. The crude product was purified by flash chromatography using petrol:ethyl acetate (10:1).
7. 3): δ 1.11 (d, 3H, J 6.7), 1.41 (s, 9H), 1.52-1.72 (m, 1H), 1.84 - 1.95 (m, 1H), 2.45 - 2.55 (m, 1H), 3.71 (s, 3H), 4.20-4.22 (m, 1H), 4.98 (d, 1H, J 8), 6.36 (d, 1H, J 15), 6.89 (dd, 1H, J 8 & 15), 7.50-7.66 (m, 3H), 7.88 (m, 2H).
8. 3): δ 1.14 (d, 3H, J 6.7), 1.44 (s, 9H), 1.6-1.8 (m, 2H), 2.45-2.55 (m, 1H), 3.74 (s, 3H), 4.20-4.4 (m, 1H), 4.98 (d, 1H, J 8), 6.36 (dd, 1H, J 1 & 15), 6.89 (dd, 1H, J 7 & 15), 7.50 -7.66 (m, 3H), 7.88 (m, 2H).
9. Clegg, W.; Elsegood, M.R.J., unpublished results. Full details of the X-ray crystal structure determination will be published separately.
10. For the most recent paper, and references to earlier work, see reference 5 above.
11. Meth-Cohn, O.; Moore, C.; Taljaard, H.C. J. Chem. Soc. Perkin Trans. I 1988, 2663-2674; Jackson, R.F.W.; Standen, S.P.; Clegg, W. J. Chem. Soc. Perkin Trans. 1 1995, 149-156.
12. Meth-Cohn, O.; Moore, C.; Taljaard, H.C. J. Chem. Soc. Perkin Trans. I 1988, 2663-2674; Jackson, R.F.W.; Standen, S.P.; Clegg, W. J. Chem. Soc. Perkin Trans. 1 1995, 149-156.
13. Devianne, G.; Escudier, J.-M.; Baltas, M.; Gorrichon, L. J. Org. Chem. 1995, 60, 7343-7347.
14. 13C NMR correlation; N.H. Rees, unpublished results. Further details will be provided in a full paper.
15. Durst, T.; Tin, K.-C.; de Reinach-Hirtzbach, F.; Decesare, J.M.; Ryan, M.D. Can. J. Chem. 1979, 57, 258-266; Tavares, D. F.; Estep, R.E.; Blezard, M. Tetrahedron Lett. 1970, 2373-2376.
16. Durst, T.; Tin, K.-C.; de Reinach-Hirtzbach, F.; Decesare, J.M.; Ryan, M.D. Can. J. Chem. 1979, 57, 258-266; Tavares, D. F.; Estep, R.E.; Blezard, M. Tetrahedron Lett. 1970, 2373-2376.
17. For examples of other reductive aminations leading to piperidine derivatives, see: Tietze, L.F.; Bachmann, J.; Schul, W. Angew. Chem. Int. Ed. Engl. 1988, 27, 971-973; Mocerino, M.; Stick, R.V. Aust. J. Chem. 1990, 43, 1183-1193; Glaenzer, B.I.; Gyoergydeak, Z.; Bernet, B.; Vasella, A. Helv. Chim. Acta 1991, 74, 343-369; Kajimoto, T.; Chen, L; Liu, K.K.-C.; Wong, C-H. J. Am. Chem. Soc. 1991, 113, 6678-6680.
18. For examples of other reductive aminations leading to piperidine derivatives, see: Tietze, L.F.; Bachmann, J.; Schul, W. Angew. Chem. Int. Ed. Engl. 1988, 27, 971-973; Mocerino, M.; Stick, R.V. Aust. J. Chem. 1990, 43, 1183-1193; Glaenzer, B.I.; Gyoergydeak, Z.; Bernet, B.; Vasella, A. Helv. Chim. Acta 1991, 74, 343-369; Kajimoto, T.; Chen, L; Liu, K.K.-C.; Wong, C-H. J. Am. Chem. Soc. 1991, 113, 6678-6680.
19. For examples of other reductive aminations leading to piperidine derivatives, see: Tietze, L.F.; Bachmann, J.; Schul, W. Angew. Chem. Int. Ed. Engl. 1988, 27, 971-973; Mocerino, M.; Stick, R.V. Aust. J. Chem. 1990, 43, 1183-1193; Glaenzer, B.I.; Gyoergydeak, Z.; Bernet, B.; Vasella, A. Helv. Chim. Acta 1991, 74, 343-369; Kajimoto, T.; Chen, L; Liu, K.K.-C.; Wong, C-H. J. Am. Chem. Soc. 1991, 113, 6678-6680.
20. For examples of other reductive aminations leading to piperidine derivatives, see: Tietze, L.F.; Bachmann, J.; Schul, W. Angew. Chem. Int. Ed. Engl. 1988, 27, 971-973; Mocerino, M.; Stick, R.V. Aust. J. Chem. 1990, 43, 1183-1193; Glaenzer, B.I.; Gyoergydeak, Z.; Bernet, B.; Vasella, A. Helv. Chim. Acta 1991, 74, 343-369; Kajimoto, T.; Chen, L; Liu, K.K.-C.; Wong, C-H. J. Am. Chem. Soc. 1991, 113, 6678-6680.