Diastereoselective arylation of enantiopure 3-bromopiperidin-2-one derived from (R)-(-)-2-phenylglycinol with organocuprate reagents

Tetrahedron Letters

Volumn 52, Issue 45, 2011, Pages 5947-5950

  Romero, Oscar ^a   Castro, Alejandro ^b   Terán, Joel L ^a   Gnecco, Dino ^a   Orea, María L ^a   Mendoza, Ángel ^a   Flores, Marcos ^c   Roa, Luis F ^d   Juárez, Jorge R ^a  

^a BENEMÉRITA UNIVERSIDAD AUTÓNOMA DE PUEBLA   (Mexico)

^b Universidad Politécnica de Tlaxcala   (Mexico)

^c Universidad Nacional Autonoma de Mexico Facultad de Quimica   (Mexico)

^d UNIVERSIDAD JUÁREZ AUTÓNOMA DE TABASCO   (Mexico)

Author keywords

[No Author keywords available]

Indexed keywords

2 PHENYLGLYCINOL; 3 BROMOPIPERIDIN 2 ONE; GLYCINE DERIVATIVE; PIPERIDONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; ARYLATION; STEREOCHEMISTRY; SUBSTITUTION REACTION;

EID: 80053589740     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2011.08.124     Document Type: Article

References (55)

1. G.M. Strunz, and J.A. Findlay A. Brossi, The Alkaloids Vol. 26 1985 Academic Press London 89 183
2. H. Takahata, and T. Momose G.A. Cordell, The Alkaloids Vol. 44 1993 Academic Press San Diego, CA 189 256
3. S. Ohmiya, K. Saito, and I. Murakoshi G.A. Cordell, The Alkaloids Vol. 47 1995 Academic Press San Diego 1 114
4. M.J. Schneider S.W. Pelletier, Alkaloids: Chemical and Biological Perspectives Vol. 10 1996 Pergamon Oxford, UK 155 299
5. R.J. Andersen, R.W.M. Van Soest, and F. Kong S.W. Pelletier, Alkaloids: Chemical and Biological Perspectives Vol. 10 1996 Pergamon Oxford, UK 301 355
6. J.W. Daly, H.M. Garraffo, and T.F. Spande S.W. Pelletier, Vol. 13 Alkaloids: Chemical and Biological Perspectives 1999 Pergamon Press NewYork 1 161
7. P.S. Watson, B. Jiang, and B. Scott Org. Lett. 2 2000 3679
8. J.P. Michael Nat. Prod. Rep. 22 2005 603 626 and previous reviews in this series
9. M. Rubiralta, E. Giralt, and A. Diez Piperidine, Structure, Preparation, Reactivity, and Synthetic Applications of Piperidine and its Derivatives 1991 Elsevier Amsterdam, The Netherlands
10. C. Kibayashi Attaur Rahman, Studies in Natural Products Chemistry. Stereoselective Synthesis (PartG) Vol.11 1992 Elsevier Amsterdam, The Netherlands 229 275
11. J. Cossy, and P. Vogel Attaur Rahman, Studies in Natural Products Chemistry. Stereoselective Synthesis (Part H) Vol. 12 1993 Elsevier Amsterdam 275 363
12. S.R. Angle, and J.G. Breitenbucher Attaur Rahman, Studies in Natural Products Chemistry (Part J) Vol.16 1995 Elsevier Amsterdam, The Netherlands 453 502
13. S. Leclerq, D. Daloze, and J.-C. Braekman Org. Prep. Proced. Int. 28 1996 501 543
14. P.D. Bailey, P.A. Millwood, and P.D. Smith Chem. Commun. 1998 633 640
15. H.-P. Husson, and J. Royer Chem. Soc. Rev. 28 1999 383 394
16. D.L. Comins J. Heterocycl. Chem. 36 1999 1491 1500
17. S. Laschat, and T. Dickner Synthesis 2000 1781 1813
18. B. Guilloteau-Bertin, D. Compre, L. Gil, C. Marazano, and B.C. Das Eur. J. Org. Chem. 2000 1391 1399
19. P.M. Weintraub, J.S. Sabol, J.M. Kane, and D.R. Borcherding Tetrahedron 59 2003 2953 2989
20. M.G.P. Buffat Tetrahedron 60 2004 1701 1729
21. L. Micouin, R. Varea, C. Riche, A. Chiaroni, J.-C. Quirion, and H.-P. Husson Tetrahedron Lett. 35 1994 2529
22. M. Amat, N. Llor, J. Hidalgo, A. Hernández, and J. Bosch Tetrahedron: Asymmetry 7 1996 977
23. M. Amat, G. Pshenichnyi, J. Bosch, E. Molins, and C. Miravitlles Tetrahedron: Asymmetry 7 1996 3091
24. A.I. Meyers, M.A. Seefeld, B.A. Lefker, J.F. Blake, and P.G. Williard J. Am. Chem. Soc. 120 1998 7429 7438
25. K. Ando, N.S. Green, Y. Li, and K.N. Houk J. Am. Chem. Soc. 121 1999 5334 5335
26. J.H. Bailey, A.T.J. Byfield, P.J. Davis, A.C. Foster, M. Leech, M.G. Moloney, M. Müller, and C.K. Prout J. Chem. Soc., Perkin Trans. 1 2000 1977 1982
27. R.C. Hughes, C.A. Dvorak, and A.I. Meyers J. Org. Chem. 66 2001 5545 5551
28. Y. Ikuta, and S. Tomoda Tetrahedron Lett. 44 2003 5931 5934
29. Y. Ikuta, and S. Tomoda Org. Lett. 6 2004 189 192
30. A.G. Brewster, S. Broady, C.E. Davies, T.D. Heightman, S.A. Hermitage, M. Hughes, M.G. Moloney, and G. Wood Org. Biomol. Chem. 2 2004 1031 1043
31. M. Amat, C. Escolano, N. Llor, O. Lozano, A. Gmez-Esqu, R. Griera, and J. Bosch Arkivoc 2005 115 123
32. I. Soteras, O. Lozano, A. Gómez-Esqué, C. Escolano, M. Orozco, M. Amat, J. Bosch, and F.J. Luque J. Am. Chem. Soc. 128 2006 6581 6588
33. I. Soteras, O. Lozano, C. Escolano, M. Orozco, M. Amat, J. Bosch, and F.J. Luque J. Org. Chem. 73 2008 7756 7763
34. For the arylation of racemic lactams, see: J. Cossy, A. de Filippis, and D.G. Pardo Synlett 2003 2171 2174
35. J. Cossy, A. de Filippis, and D.G. Pardo Org. Lett. 5 2003 3037 3079
36. A. De Filippis, D.G. Pardo, and J. Cossy Synthesis 2004 2930 2933
37. A. De Filippis, D.G. Pardo, and J. Cossy Tetrahedron 60 2004 9757 9767
38. G. Satyanarayana, and M.E. Maier Tetrahedron 64 2008 356 363
39. For the arylation of racemic amides and anilides, see: K.H. Shaughnessy, B.C. Hamann, and J.F. Hartwig J. Org. Chem. 63 1998 6546 6553
40. T.Y. Zhang, and H. Zhang Tetrahedron Lett. 43 2002 193 195
41. E. Bentz, M.G. Moloney, and S.M. Westaway Tetrahedron Lett. 45 2004 7395 7397
42. T. Hama, D.A. Culkin, and J.F. Hartwig J. Am. Chem. Soc. 128 2006 4976 4985
43. M.J. Durbin, and M.C. Willis Org. Lett. 10 2008 1413 1415
44. For the asymmetric arylation of racemic anilides, see: S. Lee, and J.F. Hartwig J. Org. Chem. 66 2001 3402 3415
45. Y.-S. Wong, C. Marazano, D. Gnecco, Y. Génisson, A. Chiaroni, and B.C. Das J. Org. Chem. 62 1997 729 733
46. M. Amat, M. Cantó, N. Llor, C. Escolano, E. Molins, E. Espinosa, and J. Bosch J. Org. Chem. 67 2002 5343 5351
47. For other enantioselective synthesis of 3-preclamol, see: S.-O. Thorberg, L. Gawell, I. Csöregh, and J.L.G. Nilsson Tetrahedron 41 1985 129 139
48. For the preparation of lactam 1, see: C.A. Castro, P.J. Juárez, D. Gnecco, J.L. Terán, A. Galindo, S. Berns, and R.G. Enríquez Tetrahedron: Asymmetry 16 2005 949 952
49. L. Micouin, M. Bonin, M.-P. Cherrier, A. Mazurier, A. Tomas, J.-C. Quirion, and H.-P. Husson Tetrahedron Lett. 52 1996 7719 7726
50. For substitution reactions of the lactam 2 with different heteroatom and electron-rich carbon nucleophiles, see: R. Rodrguez, M.A. Estiarte, A. Diez, M. Rubiralta, A. Colell, C. Garcaí-Ruíz, and J. Fernández- Checa Tetrahedron 52 1996 7727 7736 See also: Ref. 7
51. 2 complex, see
52. M. Eriksson, A. Hjelmencrantz, M. Nilsson, and T. Olsson Tetrahedron 51 1995 12631 12644
53. M. Eriksson, T. Iliefski, M. Nilsson, and T. Olsson J. Org. Chem. 62 1997 182 187
54. For a discussion on the reactivity of organocuprates in dimethyl sulfide, see: S.H. Bertz, and G. Dabbagh Tetrahedron 45 1989 425 434
55. Crystal structure was deposited at the Cambridge Crystallographic Data Centre. Deposit number: CCDC831758.