Catalytic enantioselective [2+2]-cycloaddition reaction of 2-methoxycarbonyl-2-cyclopenten-1-one by chiral copper catalyst

Tetrahedron

Volumn 62, Issue 14, 2006, Pages 3380-3388

  Takenaka, Yosuke ^a   Ito, Hisanaka ^a   Hasegawa, Mineki ^a   Iguchi, Kazuo ^a  

^a TOKYO UNIVERSITY OF PHARMACY AND LIFE SCIENCES   (Japan)

Author keywords

2+2 Cycloaddition reaction; Copper salt; Ligand

Indexed keywords

2 METHOXYCARBONYL 2 CYCLOPENTEN 1; CARBONYL DERIVATIVE; COPPER; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; CHIRALITY; CYCLOADDITION; ENANTIOSELECTIVITY; PRIORITY JOURNAL;

EID: 33644902714     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2006.01.050     Document Type: Article

References (48)

1. For recent reviews on cyclobutane derivatives, see: (a) M.T. Crimmins B.M. Trost I. Fleming Comprehensive Organic Synthesis Vol. 5 1991 Pergamon Oxford Chapter 2.3
2. E. Lee-Ruff, and G. Mladenova Chem. Rev. 103 2003 1449 1483
3. J.C. Namyslo, and D.E. Kaufmann Chem. Rev. 103 2003 1485 1537
4. For examples, see: (a) A.I. Meyers, M.A. Tschantz, and G.P. Brengel J. Org. Chem. 60 1995 4359 4362
5. M.D. Groaning, G.P. Brengel, and A.I. Meyers Tetrahedron 57 2001 2635 2642
6. S. Ahmad Tetrahedron Lett. 32 1991 6997 7000
7. R.F. Sweis, M.P. Schramm, and S.A. Kozmin J. Am. Chem. Soc. 126 2004 7442 7443
8. K. Takao, H. Saegusa, T. Tsujita, T. Washizawa, and K. Tadano Tetrahedron Lett. 46 2005 5815 5818
9. K. Takasu, M. Ueno, K. Inanaga, and M. Ihara J. Org. Chem. 69 2004 517 521
10. K. Takasu, S. Nagao, M. Ueno, and M. Ihara Tetrahedron 60 2004 2071 2078
11. Lewis acid-catalyzed [2+2]-cycloaddition of γ,γ- dialkoxyallylic zirconium species to α,β-unsaturated carbonyl compounds, see: H. Ito, A. Sato, and T. Taguchi Tetrahedron Lett. 40 1999 3217 3220
12. For review, see: (a) Y. Hayashi, and K. Narasaka E.N. Jacobsen A. Pfalts H. Yamamoto Comprehensive Asymmetric Catalysis 1999 Springer Berlin 1255 1269
13. See: also; (b) Y. Hayashi, and K. Narasaka Chem. Lett. 1989 793 796
14. Y. Ichikawa, A. Narita, A. Shiozawa, Y. Hayashi, and K. Narasaka J. Chem. Soc., Chem. Commun. 1989 1919 1921
15. K. Narasaka, Y. Hayashi, H. Shimadzu, and S. Niihara J. Am. Chem. Soc. 114 1992 8869 8885
16. K. Narasaka, H. Kusama, and Y. Hayashi Bull. Chem. Soc. Jpn. 64 1991 1471 1478
17. Y. Hayashi, K. Otaka, N. Saito, and K. Narasaka Bull. Chem. Soc. Jpn. 64 1991 2122 2127
18. Y. Hayashi, and K. Narasaka Chem. Lett. 1990 1295 1298
19. K. Narasaka, K. Hayashi, and Y. Hayashi Tetrahedron 50 1994 4529 4542
20. For examples of diastereoselective addition of nucleophile to chiral 2-cyclopentenecarboxylate, see: (a) V. Berl, G. Helmchen, and S. Preston Tetrahedron Lett. 35 1994 233 236
21. E. Urban, G. Knühl, and G. Helmchen Tetrahedron Lett. 36 1995 7229 7232
22. E. Urban, G. Knühl, and G. Helmchen Tetrahedron 51 1995 13031 13038
23. E. Urban, G. Knühl, and G. Helmchen Tetrahedron 52 1996 971 986
24. H. Spreitzer, A. Pichler, W. Holzer, I. Toth, and B. Zuchart Helv. Chim. Acta 80 1997 139 145
25. H. Spreitzer, A. Pichler, W. Holzer, and C. Schlager Helv. Chim. Acta 81 1998 40 45
26. D. Chapdelaine, J. Belzile, and P. Deslongchamps J. Org. Chem. 67 2002 5669 5672
27. For examples of diastereoselective addition of chiral nucleophile to 2-cyclopentenecarboxylate, see: (a) D. Enders, and A. Kaiser Liebigs Ann. 1997 485 493
28. D. Enders, and A. Kaiser Heterocycles 46 1997 631 635
29. For examples of enantioselective addition of nucleophile to 2-cyclopentenecarboxylate using chiral catalyst, see: (a) A. Bernardi, K. Karamfilova, G. Boschin, and C. Scolastico Tetrahedron Lett. 36 1995 1363 1364
30. A. Bernardi, G. Colombo, and C. Scolastico Tetrahedron Lett. 37 1996 8921 8924
31. A. Bernardi, K. Karamfilova, S. Sanguinetti, and C. Scolastico Tetrahedron 53 1997 13009 13026
32. D.A. Evans, T. Rovis, M.C. Kozlowski, C.W. Downey, and J.S. Tedrow J. Am. Chem. Soc. 122 2000 9134 9142
33. For examples of asymmetric cyclopropanation of 2-cyclopentenecarboxylate, see: (a) S. Fioravanti, A. Morreale, L. Pellacani, and P.A. Tardella J. Org. Chem. 67 2002 4972 4974
34. S. Fioravanti, A. Morreale, L. Pellacani, and P.A. Tardella Tetrahedron Lett. 44 2003 3031 3034
35. One example of enantioselective [2+2]-cycloaddition of 2-cyclopentenecarboxylate was already reported as a key step of a total synthesis of tricycloclavulone by our group, see: (a) H. Ito, M. Hasegawa, Y. Takenaka, T. Kobayashi, and K. Iguchi J. Am. Chem. Soc. 126 2004 4520 4521
36. See also, (b) H. Ito, T. Kobayashi, M. Hasegawa, and K. Iguchi Tetrahedron Lett. 44 2003 1259 1261
37. A. Bernardi, K. Karamfilova, S. Sanguinetti, and C. Scolastico Tetrahedron 53 1997 13009 13026
38. N.L. Bauld, J.T. Aplin, W. Yeuh, and A. Loinaz J. Am. Chem. Soc. 119 1997 11381 11389
39. W.E. Parham, and J. Heberling J. Am. Chem. Soc. 77 1955 1175 1177
40. W.E. Parharm, and P.L. Stright J. Am. Chem. Soc. 78 1956 4783 4787
41. D.A. Evans, D.M. Barnes, J.S. Johnson, T. Lectka, P. von Matt, S.J. Miller, J.A. Murry, R.D. Norcross, E.A. Shaughnessy, and K.R. Campos J. Am. Chem. Soc. 121 1999 7582 7594
42. S. Matsukawa, and K. Mikami Tetrahedron: Asymmetry 8 1997 815 816
43. O. Mitsunobu Synthesis 1981 1 28
44. For 23a, see: (a) S. Casson, P. Kocienski, G. Reid, N. Smith, J.M. Street, and M. Webster Synthesis 1994 1301 1309
45. For 23b, see: (b) H. Kleijn, and P. Vermeer J. Org. Chem. 50 1985 5143 5148
46. For 23c, see: (c) E. Schaumann, H. Behr, and J. Lindstaedt Chem. Ber. 116 1983 66 73
47. See also, R.K. Dieter J. Org. Chem. 65 2000 8715 8724
48. H. Kuritani, Y. Takaoka, and K. Shingu J. Org. Chem. 44 1979 452 454