Copper-catalyzed enantioselective allylic alkylation ring-opening reactions of small-ring heterocycles with hard alkyl metals

New Journal of Chemistry

Volumn 28, Issue 6, 2004, Pages 657-665

  Pineschi, Mauro ^a  

^a UNIVERSITY OF PISA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYL GROUP; ALLYL COMPOUND; AZIRIDINE DERIVATIVE; COPPER; EPOXIDE; HETEROCYCLIC COMPOUND; LIGAND; ORGANOMETALLIC COMPOUND; PHOSPHORAMIDIC ACID DERIVATIVE; PHOSPHORUS; ZINC DERIVATIVE;

ALKYLATION; CATALYSIS; CHEMICAL STRUCTURE; CHIRALITY; DISTILLATION; ELECTRON; ELIMINATION REACTION; ENANTIOSELECTIVITY; FILTRATION; PRIORITY JOURNAL; RACEMIZATION; REDUCTION KINETICS; REVIEW; RING OPENING; STEREOCHEMISTRY; SUBSTITUTION REACTION;

EID: 3042822552     PISSN: 11440546     EISSN: None     Source Type: Journal    
DOI: 10.1039/b314951j     Document Type: Review

References (81)

1. B. M. Trost and C. Lee, in Catalytic Asymmetric Synthesis, ed. I. Ojima, VCH Publishers, New York, 2nd edn., 2000, p. 593.
2. B. M. Trost and M. L. Crawley, Chem. Rev., 2003, 103, 2921.
3. A. S. E. Karlström and J.-E. Bäckvall, in Modern Organocopper Chemistry, ed. N. Krause, Wiley-VCH, Weinheim, 2001, p. 259 and references cited therein.
4. B. Breit and P. Demel, in Modern Organocopper Chemistry, ed. N. Krause, Wiley-VCH, Weinheim, 2001, p. 210 and references cited therein.
5. (a) G. J. Meuzelaar, A. S. E. Karlström, M. van Klaveren, E. S. M. Persson, A. del Villar, G. Van Koten and J.-E. Bäckvall, Tetrahedron, 2000, 56, 2895;
6. (b) A. S. E. Karlström, F. F. Huerta, G. J. Meuzelaar and J.-E. Bäckvall, Synlett, 2001, 923.
7. (a) A. Alexakis, C. Malan, L. Lea, C. Benhaim and X. Fournioux, Synlett, 2001, 927;
8. (b) A. Alexakis and K. Croset, Org. Lett., 2002, 4, 4147.
9. F. Dübner and P. Knochel, Angew. Chem., Int. Ed., 1999, 38, 379.
10. H. Malda, A. W. van Zijl, L. A. Arnold and B. L. Feringa, Org. Lett., 2001, 3, 1169.
11. C. A. Luchaco-Cullis, H. Mizutani, K. E. Murphy and A. H. Hoveyda, Angew. Chem., Int. Ed., 2001, 40, 1456.
12. K. E. Murphy and A. H. Hoveyda, J. Am. Chem. Soc., 2003, 125, 4690.
13. U. Piarulli, P. Daubos, C. Claverie, M. Roux and C. Gennari, Angew. Chem., Int. Ed., 2003, 42, 234.
14. For a review of allylic epoxide ring openings with organocuprates, see: (a) J. A. Marshall, Chem. Rev., 1989, 89, 1503 and references cited therein; for selected examples of allylic aziridine ring openings with organocuprates, see (b) P. Wipf and P. C. Fritch, J. Org. Chem., 1994, 59, 4875; (c) T. Ibuka, K. Nakai, H. Habashita, Y. Hotta, N. Fujii, N. Mimura, Y. Miwa, T. Taga and Y. Yamamoto, Angew. Chem., Int. Ed. Engl., 1994, 33, 652; (d) A. A. Cantrill, A. N. Jarvis, H. M. I. Osborn, A. Ouadi and J. B. Sweeney, Synlett, 1996, 847; (e) A. Toda, H. Aoyama, N. Mimura, H. Ohno, N. Fujii and T. Ibuka, J. Org. Chem., 1998, 63, 7053 and references therein; (f) C. S. Penkett and I. D. Simpson, Tetrahedron Lett., 2001, 42, 1179.
15. For a review of allylic epoxide ring openings with organocuprates, see: (a) J. A. Marshall, Chem. Rev., 1989, 89, 1503 and references cited therein; for selected examples of allylic aziridine ring openings with organocuprates, see (b) P. Wipf and P. C. Fritch, J. Org. Chem., 1994, 59, 4875; (c) T. Ibuka, K. Nakai, H. Habashita, Y. Hotta, N. Fujii, N. Mimura, Y. Miwa, T. Taga and Y. Yamamoto, Angew. Chem., Int. Ed. Engl., 1994, 33, 652; (d) A. A. Cantrill, A. N. Jarvis, H. M. I. Osborn, A. Ouadi and J. B. Sweeney, Synlett, 1996, 847; (e) A. Toda, H. Aoyama, N. Mimura, H. Ohno, N. Fujii and T. Ibuka, J. Org. Chem., 1998, 63, 7053 and references therein; (f) C. S. Penkett and I. D. Simpson, Tetrahedron Lett., 2001, 42, 1179.
16. For a review of allylic epoxide ring openings with organocuprates, see: (a) J. A. Marshall, Chem. Rev., 1989, 89, 1503 and references cited therein; for selected examples of allylic aziridine ring openings with organocuprates, see (b) P. Wipf and P. C. Fritch, J. Org. Chem., 1994, 59, 4875; (c) T. Ibuka, K. Nakai, H. Habashita, Y. Hotta, N. Fujii, N. Mimura, Y. Miwa, T. Taga and Y. Yamamoto, Angew. Chem., Int. Ed. Engl., 1994, 33, 652; (d) A. A. Cantrill, A. N. Jarvis, H. M. I. Osborn, A. Ouadi and J. B. Sweeney, Synlett, 1996, 847; (e) A. Toda, H. Aoyama, N. Mimura, H. Ohno, N. Fujii and T. Ibuka, J. Org. Chem., 1998, 63, 7053 and references therein; (f) C. S. Penkett and I. D. Simpson, Tetrahedron Lett., 2001, 42, 1179.
17. For a review of allylic epoxide ring openings with organocuprates, see: (a) J. A. Marshall, Chem. Rev., 1989, 89, 1503 and references cited therein; for selected examples of allylic aziridine ring openings with organocuprates, see (b) P. Wipf and P. C. Fritch, J. Org. Chem., 1994, 59, 4875; (c) T. Ibuka, K. Nakai, H. Habashita, Y. Hotta, N. Fujii, N. Mimura, Y. Miwa, T. Taga and Y. Yamamoto, Angew. Chem., Int. Ed. Engl., 1994, 33, 652; (d) A. A. Cantrill, A. N. Jarvis, H. M. I. Osborn, A. Ouadi and J. B. Sweeney, Synlett, 1996, 847; (e) A. Toda, H. Aoyama, N. Mimura, H. Ohno, N. Fujii and T. Ibuka, J. Org. Chem., 1998, 63, 7053 and references therein; (f) C. S. Penkett and I. D. Simpson, Tetrahedron Lett., 2001, 42, 1179.
18. For a review of allylic epoxide ring openings with organocuprates, see: (a) J. A. Marshall, Chem. Rev., 1989, 89, 1503 and references cited therein; for selected examples of allylic aziridine ring openings with organocuprates, see (b) P. Wipf and P. C. Fritch, J. Org. Chem., 1994, 59, 4875; (c) T. Ibuka, K. Nakai, H. Habashita, Y. Hotta, N. Fujii, N. Mimura, Y. Miwa, T. Taga and Y. Yamamoto, Angew. Chem., Int. Ed. Engl., 1994, 33, 652; (d) A. A. Cantrill, A. N. Jarvis, H. M. I. Osborn, A. Ouadi and J. B. Sweeney, Synlett, 1996, 847; (e) A. Toda, H. Aoyama, N. Mimura, H. Ohno, N. Fujii and T. Ibuka, J. Org. Chem., 1998, 63, 7053 and references therein; (f) C. S. Penkett and I. D. Simpson, Tetrahedron Lett., 2001, 42, 1179.
19. For a review of allylic epoxide ring openings with organocuprates, see: (a) J. A. Marshall, Chem. Rev., 1989, 89, 1503 and references cited therein; for selected examples of allylic aziridine ring openings with organocuprates, see (b) P. Wipf and P. C. Fritch, J. Org. Chem., 1994, 59, 4875; (c) T. Ibuka, K. Nakai, H. Habashita, Y. Hotta, N. Fujii, N. Mimura, Y. Miwa, T. Taga and Y. Yamamoto, Angew. Chem., Int. Ed. Engl., 1994, 33, 652; (d) A. A. Cantrill, A. N. Jarvis, H. M. I. Osborn, A. Ouadi and J. B. Sweeney, Synlett, 1996, 847; (e) A. Toda, H. Aoyama, N. Mimura, H. Ohno, N. Fujii and T. Ibuka, J. Org. Chem., 1998, 63, 7053 and references therein; (f) C. S. Penkett and I. D. Simpson, Tetrahedron Lett., 2001, 42, 1179.
20. B. H. Lipshutz, K. Woo, T. Gross, D. J. Buzard and R. Tirado, Synlett, 1997, 477.
21. For reviews, see: (a) P. Chiu and M. Lautens, Top. Curr. Chem., 1997, 190, 1; (b) M. Lautens, Synlett, 1993, 177.
22. For reviews, see: (a) P. Chiu and M. Lautens, Top. Curr. Chem., 1997, 190, 1; (b) M. Lautens, Synlett, 1993, 177.
23. For a recent rview, see: M. Lautens, K. Fagnou and S. Hiebert, Acc. Chem. Res., 2003, 36, 48.
24. M. Lautens, J.-L. Renaud and S. Hiebert, J. Am. Chem Soc., 2000, 122, 1804.
25. M. Lautens, C. Dockendorff, K. Fagnou and A. Malicki, Org. Lett., 2002, 4, 1311.
26. K. Fagnou and M. Lautens, Chem. Rev., 2003, 103, 169.
27. D. B. Millward, G. Sammis and R. M. Waymouth, J. Org. Chem., 2000, 65, 3902.
28. (a) A. H. M. de Vries, A. Meetsma and B. L. Feringa, Angew. Chem., Int. Ed. Engl., 1996, 35, 2374;
29. (b) B. L. Feringa, M. Pineschi, L. A. Arnold, R. Imbos and A. H. M. de Vries, Angew. Chem., Int. Ed., 1997, 36, 2620; ;
30. for overviews of phosphoramidites in catalytic asymmetric conjugate additions, see (c) B. L. Feringa, Acc. Chem. Res., 2000, 33, 346; (d) A. Alexakis and C. Benhaim, Eur. J. Org. Chem., 2002, 3221.
31. for overviews of phosphoramidites in catalytic asymmetric conjugate additions, see (c) B. L. Feringa, Acc. Chem. Res., 2000, 33, 346; (d) A. Alexakis and C. Benhaim, Eur. J. Org. Chem., 2002, 3221.
32. F. Badalassi, P. Crotti, F. Macchia, M. Pineschi, A. Arnold and B. L. Feringa, Tetrahedron Lett., 1998, 39, 7795.
33. D. J. Berrisford, C. Bolm and K. B. Sharpless, Angew. Chem., Int. Ed. Engl., 1995, 34, 1059.
34. F. Bertozzi, P. Crotti, B. L. Feringa, F. Macchia and M. Pineschi, Synthesis, 2001, 483 and references cited therein.
35. For an alternative approach based on the KR of racemic 4-methyl-2-cyclohexen-1-one, see: R. Naasz, L. A. Arnold, A. J. Minnaard and B. L. Feringa, Angew. Chem., Int. Ed., 2001, 40, 927.
36. P. Knochel, J. J. Almena Perea and P. Jones, Tetrahedron, 1998, 54, 8275.
37. F. Bertozzi, P. Crotti, F. Del Moro, V. Di Bussolo, F. Macchia and M. Pineschi, Eur. J. Org. Chem., 2003, 1264.
38. M. Lautens, S. Hiebert and J.-L. Renaud, J. Am. Chem Soc., 2001, 123, 6834.
39. 2 (3.0 mol %) and chiral ligand L2 (7 mol %) afforded, after 60 h at r.t., unreacted 16 with 92% ee at 56% conversion and exclusively anti-dihydronaphthol 18 (86% ee).
40. F. Bertozzi, M. Pineschi, F. Macchia, L. A. Arnold, A. J. Minnaard and B. L. Feringa, Org. Lett., 2002, 4, 2703.
41. R. G. Arrayas, S. Cabrera and J. C. Carretero, Org. Lett., 2003, 5, 1333.
42. For some recent reports, see: (a) B. Olofsson and P. Somfai, J. Org. Chem., 2003, 68, 2514 and references therein; (b) B. J. Paul, E. Hobbs, P. Buccino and T. Hudlicky, Tetrahedron Lett., 2001, 42, 6433; (c) D. C. D. Butler, G. A. Inman and H. Alper, J. Org. Chem., 2000, 65, 5887.
43. For some recent reports, see: (a) B. Olofsson and P. Somfai, J. Org. Chem., 2003, 68, 2514 and references therein; (b) B. J. Paul, E. Hobbs, P. Buccino and T. Hudlicky, Tetrahedron Lett., 2001, 42, 6433; (c) D. C. D. Butler, G. A. Inman and H. Alper, J. Org. Chem., 2000, 65, 5887.
44. For some recent reports, see: (a) B. Olofsson and P. Somfai, J. Org. Chem., 2003, 68, 2514 and references therein; (b) B. J. Paul, E. Hobbs, P. Buccino and T. Hudlicky, Tetrahedron Lett., 2001, 42, 6433; (c) D. C. D. Butler, G. A. Inman and H. Alper, J. Org. Chem., 2000, 65, 5887.
45. F. Gini, F. Del Moro, F. Macchia and M. Pineschi, Tetrahedron Lett., 2003, 44, 8559.
46. For a review of enantioselective desymmetrization reactions, see: M. C. Willis, J. Chem. Soc., Perkin Trans. 1, 1999, 1765.
47. F. Bertozzi, P. Crotti, F. Macchia, M. Pineschi, A. Arnold and B. L. Feringa, Org. Lett., 2000, 2, 933.
48. For the first preparation of chiral ligand L3, see ref. 20b. Chiral ligand L3 has recently been used in the iridium-catalyzed allylic etherification and animation of achiral allylic esters: (a) T. Ohmura and J. F. Hartwig, J. Am. Chem. Soc., 2002, 124, 15 164; (b) F. Lopez, T. Ohmura and J. F. Hartwig, J. Am. Chem. Soc., 2003, 125, 3426.
49. For the first preparation of chiral ligand L3, see ref. 20b. Chiral ligand L3 has recently been used in the iridium-catalyzed allylic etherification and animation of achiral allylic esters: (a) T. Ohmura and J. F. Hartwig, J. Am. Chem. Soc., 2002, 124, 15 164; (b) F. Lopez, T. Ohmura and J. F. Hartwig, J. Am. Chem. Soc., 2003, 125, 3426.
50. For reviews, see: (a) T. C. Bruice and P. Y. Bruice, Acc. Chem. Res., 1976, 9, 378; (b) D. R. Boyd and D. M. Jerina, in Small Ring Heterocycles, Part 3, Chemistry of Heterocyclic Compounds, ed. A. Hassner, Wiley, New York, 1985, vol. 42, p. 197.
51. For reviews, see: (a) T. C. Bruice and P. Y. Bruice, Acc. Chem. Res., 1976, 9, 378; (b) D. R. Boyd and D. M. Jerina, in Small Ring Heterocycles, Part 3, Chemistry of Heterocyclic Compounds, ed. A. Hassner, Wiley, New York, 1985, vol. 42, p. 197.
52. See, for example: A. M. Jeffrey, H. J. C. Yeh, D. M. Jerina, R. M. DeMarinis, C. H. Foster, D. E. Piccolo and G. A. Berchtold, J. Am. Chem. Soc., 1974, 96, 6929.
53. F. Bertozzi, P. Crotti, F. Del Moro, B. L. Feringa, F. Macchia and M. Pineschi, Chem. Commun., 2001, 2606 and references therein.
54. T. Matsuda and M. Sugishita, Bull. Chem. Soc. Jpn., 1967, 40, 174.
55. M. Ogawa, M. Sugishita, M. Takagi and T. Matsuda, Tetrahedron, 1975, 31, 299.
56. M. J. Miller, M. H. Lyttle and A. Streitwieser, Jr., J. Org. Chem., 1981, 46, 1977.
57. For a review regarding the structure and reactivity of cyanocuprates, see: N. Krause, Angew. Chem., Int. Ed., 1999, 38, 79.
58. F. Del Moro, P. Crotti, V. Di Bussolo, F. Macchia and M. Pineschi, Org. Lett., 2003, 5, 1971.
59. The maximum tolerated deviation from the perfect alignment seems to be ca. 30°. In general, the prerequisite for an allylic alkylation to occur is the ability of the system to attain a conformation in which the π orbitals of the double bond and the σ bond connecting the leaving group are aligned. For example, see: C. N. Farthing and P. Kocovsky, J. Am. Chem. Soc., 1998, 120, 6661 and pertinent references therein.
60. F. Bertozzi, M. Pineschi, F. Macchia, L. A. Arnold, A. J. Minnaard and B. L. Feringa, unpublished results.
61. For a recent review on kinetic resolution, see: J. M. Keith, J. F. Larrow and E. N. Jacobsen, Adv. Synth. Catal., 2001, 1, 5 and references therein.
62. For reviews, see: (a) J. R. Dehli and V. Gotor, Chem. Soc. Rev., 2002, 31, 365; (b) J. Eames, Angew. Chem., Int. Ed., 2000, 39, 885.
63. For reviews, see: (a) J. R. Dehli and V. Gotor, Chem. Soc. Rev., 2002, 31, 365; (b) J. Eames, Angew. Chem., Int. Ed., 2000, 39, 885.
64. (a) M. P. Doyle, A. B. Dyatkin, A. V. Kalinin, Q. A. Ruppar, S. F. Martin, M. R. Spaller and S. Liras, J. Am. Chem. Soc., 1995, 117, 11 021;
65. (b) K. Tanaka and G. C. Fu, J. Am. Chem. Soc., 2003, 125, 8078.
66. For the only previous example of a RKR making use of a hard alkyl metal (EtMgBr), see: M. S. Visser and A. H. Hoveyda, Tetrahedron, 1995, 51, 4383.
67. F. Bertozzi, P. Crotti, F. Macchia, M. Pineschi and B. L. Feringa, Angew. Chem., Int. Ed., 2001, 40, 930 and references therein.
68. M. Pineschi, F. Del Moro, P. Crotti, V. Di Bussolo and F. Macchia, J. Org. Chem., 2004, 69, 2099.
69. For reviews on enantioselective formation of quaternary carbon stereocenters, see: (a) E. J. Corey and A. Guzmȧn-Pérez, Angew. Chem., Int. Ed., 1998, 37, 388; (b) J. Christoffers and A. Mann, Angew. Chem., Int. Ed., 2001, 40, 4591.
70. For reviews on enantioselective formation of quaternary carbon stereocenters, see: (a) E. J. Corey and A. Guzmȧn-Pérez, Angew. Chem., Int. Ed., 1998, 37, 388; (b) J. Christoffers and A. Mann, Angew. Chem., Int. Ed., 2001, 40, 4591.
71. For a related explanation, see: T. L. Underiner, S. D. Paisley, J. Schmitter, L. Leshesky and H. L. Goering, J. Org. Chem., 1989, 54, 2369.
72. For a recent review, see: E. Nakamura and S. Mori, Angew. Chem., Int. Ed., 2000, 39, 3750.
73. A. S. E. Karlström and J.-E. Bäckwall, Chem.-Eur. J., 2001, 7, 1981 and references therein.
74. E. Nakamura, M. Yamanaka and S. Mori, J. Am. Chem Soc., 2000, 122, 1826.
75. 57 The interconversion between the regioisomeric (σ-allyl) copper(III) complexes of type H-J could also be reasonably explained by the intervention of suprafacial 1,3-shifts.
76. For an alternative explanation, see: M. Ito, M. Matsuumi, M. G. Murugesh and Y. Kobayashi, J. Org. Chem., 2001, 66, 5881 and references therein.
77. E. N. Jacobsen and M. H. Wu, in Comprehensive Asymmetric Catalysis, eds. E. N. Jacobsen, A. Pfaltz and H. Yamamoto, Springer, New York, 1999, ch. 35.
78. 2-hybridized organometallic reagents, see: (a) M. Mizuno, M. Kanai, M. A. Iida and K. Tomioka, Tetrahedron, 1997, 53, 10699; (b) A. Alexakis, E. Vrancken and P. Mangeney, Synlett, 1998, 1165; (c) N. Oguni, Y. Miyagi and K. Itoh, Tetrahedron Lett., 1998, 39, 9023.
79. 2-hybridized organometallic reagents, see: (a) M. Mizuno, M. Kanai, M. A. Iida and K. Tomioka, Tetrahedron, 1997, 53, 10699; (b) A. Alexakis, E. Vrancken and P. Mangeney, Synlett, 1998, 1165; (c) N. Oguni, Y. Miyagi and K. Itoh, Tetrahedron Lett., 1998, 39, 9023.
80. 2-hybridized organometallic reagents, see: (a) M. Mizuno, M. Kanai, M. A. Iida and K. Tomioka, Tetrahedron, 1997, 53, 10699; (b) A. Alexakis, E. Vrancken and P. Mangeney, Synlett, 1998, 1165; (c) N. Oguni, Y. Miyagi and K. Itoh, Tetrahedron Lett., 1998, 39, 9023.
81. For the catalytic asymmetric ring opening of activated aziridines, see: P. Müller and P. Nury, Org. Lett., 1999, 1, 439.