Concise synthesis of trans- and cis-3,4-disubstituted piperidines based on regio- and stereoselective allylation of cyclopentenyl esters

Tetrahedron Letters

Volumn 45, Issue 43, 2004, Pages 8065-8068

  Igarashi, Junji ^a   Ishiwata, Hiroyuki ^a   Kobayashi, Yuichi ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

3,4 Disubstituted piperidine; Cyclopenten 1,3 diol monoacetate; Paroxetine

Indexed keywords

COPPER DERIVATIVE; ESTER DERIVATIVE; MAGNESIUM DERIVATIVE; PIPERIDINE DERIVATIVE; REAGENT;

ALLYLATION; ARTICLE; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; ISOMERIZATION; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 4644240240     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.08.174     Document Type: Article

References (49)

1. For recent reviews: P.M. Weintraub, J.S. Sabol, J.M. Kane, and D.R. Borcherding Tetrahedron 59 2003 2953 2989
2. B. Danieli, G. Lesma, D. Passarella, and A. Silvani Curr. Org. Chem. 4 2000 231 261
3. S. Laschat, and T. Dickner Synthesis 2000 1781 1813
4. M.D. Groaning, and A.I. Meyers Tetrahedron 56 2000 9843 9873
5. A.I. Meyers, C.J. Andres, J.E. Resek, C.C. Woodall, M.A. McLaughlin, P.H. Lee, and D.A. Price Tetrahedron 55 1999 8931 8952
6. T. Fujii, and M. Ohba Heterocycles 47 1998 525 539
7. I.T. Raheem, S.N. Goodman, and E.N. Jacobsen J. Am. Chem. Soc. 126 2004 706 707
8. J. Igarashi, M. Katsukawa, Y.-G. Wang, H.P. Acharya, and Y. Kobayashi Tetrahedron Lett. 45 2004 3783 3786
9. M.S. Taylor, and E.N. Jacobsen J. Am. Chem. Soc. 125 2003 11204 11205
10. J.T. Williams, P.S. Bahia, and J.S. Snaith Org. Lett. 4 2002 3727 3730
11. A.P. Kozikowski, G.L. Araldi, J. Boja, W.M. Meil, K.M. Johnson, J.L. Flippen-Anderson, C. George, and E. Saiah J. Med. Chem. 41 1998 1962 1969
12. Y. Hirai, T. Terada, T. Yamazaki, and T. Momose J. Chem. Soc., Perkin Trans. 1 1992 517 524
13. M. Ihara, K. Yasui, N. Taniguchi, and K. Fukumoto J. Chem. Soc., Perkin Trans. 1 1990 1469 1476
14. T. Fujii, M. Ohba, and J. Sakaguchi Chem. Pharm. Bull. 35 1987 3628 3640
15. R.L. Funk, and J.D. Munger Jr. J. Org. Chem. 49 1984 4319 4322
16. T. Imanishi, M. Inoue, Y. Wada, and M. Hanaoka Chem. Pharm. Bull. 30 1982 1925 1928
17. S. Takano, M. Takahashi, S. Hatakeyama, and K. Ogasawara J. Chem. Soc., Chem. Commun. 1979 556 557
18. M.R. Uskokovic, T. Henderson, C. Reese, H.L. Lee, G. Grethe, and J. Gutzwiller J. Am. Chem. Soc. 100 1978 571 576
19. G. Stork, and S.M. McElvain J. Am. Chem. Soc. 68 1946 1053 1057
20. R.B. Woodward, and W.E. Doering J. Am. Chem. Soc. 67 1945 860 874
21. T.A. Johnson, M.D. Curtis, and P. Beak J. Am. Chem. Soc. 123 2001 1004 1005
22. T.A. Johnson, D.O. Jang, B.W. Slafer, M.D. Curtis, and P. Beak J. Am. Chem. Soc. 124 2002 11689 11698
23. M. Amat, M. Cantó, N. Llor, V. Ponzo, M. Pérez, and J. Bosch Angew. Chem., Int. Ed. 41 2002 335 338
24. M. Amat, M. Pérez, N. Llor, and J. Bosch Org. Lett. 4 2002 2787 2790
25. M. Amat, M. Pérez, N. Llor, J. Bosch, E. Lago, and E. Molins Org. Lett. 3 2001 611 614
26. H. Hattori, A.A. Abbas, and Y. Kobayashi Chem. Commun. 2004 884 885
27. T. Ainai, M. Ito, and Y. Kobayashi Tetrahedron Lett. 44 2003 3983 3986
28. Y. Kobayashi, M.G. Murugesh, M. Nakano, E. Takahisa, S.B. Usmani, and T. Ainai J. Org. Chem. 67 2002 7110 7123
29. M. Ito, M. Matsuumi, M.G. Murugesh, and Y. Kobayashi J. Org. Chem. 66 2001 5881 5889
30. Y. Kobayashi Curr. Org. Chem. 7 2003 133 147
31. H.P. Acharya, and Y. Kobayashi Tetrahedron Lett. 45 2004 1199 1202
32. T. Ainai, Y.-G. Wang, Y. Tokoro, and Y. Kobayashi J. Org. Chem. 69 2004 655 659
33. T. Ainai, M. Matsuumi, and Y. Kobayashi J. Org. Chem. 68 2003 7825 7832
34. Y. Kobayashi, M. Ito, and J. Igarashi Tetrahedron Lett. 43 2002 4829 4832
35. K. Tamao, and N. Ishida Tetrahedron Lett. 25 1984 4245 4248
36. Recent syntheses: G. Hughes, M. Kimura, and S.L. Buchwald J. Am. Chem. Soc. 125 2003 11253 11258
37. G. de Gonzalo, R. Brieva, V.M. Sánchez, M. Bayod, and V. Gotor J. Org. Chem. 68 2003 3333 3336
38. K. Takasu, N. Nishida, and M. Ihara Tetrahedron Lett. 44 2003 7429 7432
39. K.S.K. Murthy, A.W. Rey, and M. Tjepkema Tetrahedron Lett. 44 2003 5355 5358
40. D.A. Greenhalgh, and N.S. Simpkins Synlett 2002 2074 2076
41. J. Cossy, O. Mirguet, D.G. Pardo, and J.-R. Desmurs Eur. J. Org. Chem. 2002 3543 3551
42. J. Cossy, O. Mirguet, D.G. Pardo, and J.-R. Desmurs Tetrahedron Lett. 42 2001 7805 7807
43. T. Senda, M. Ogasawara, and T. Hayashi J. Org. Chem. 66 2001 6852 6856
44. M. Amat, J. Bosch, J. Hidalgo, M. Cánto, M. Pérez, N. Llor, E. Molins, C. Miravitlles, M. Orozco, and J. Luque J. Org. Chem. 65 2000 3074 3084
45. M.S. Yu, I. Lantos, Z.-Q. Peng, J. Yu, and T. Cacchio Tetrahedron Lett. 41 2000 5647 5651
46. In THF, the 1:1 or 2:1 reagents from BuMgX and CuCN were less reactive or less selective, providing ca. 30% yield of the butylation product or ca. 2:1 regioselection
47. 4OH to afford trans-3b (87 mg) in 97% yield after chromatography on silica gel
48. 2 group, we did not examine it for reasons of toxicity
49. Butylation of 15 afforded trans-3d (see Scheme 1 for the structure), which produced the corresponding piperidine as well