Enantioselective synthesis of 2-aryl cyclopentanones by asymmetric epoxidation and epoxide rearrangement

Angewandte Chemie - International Edition

Volumn 45, Issue 9, 2006, Pages 1429-1432

  Shen, Yu Mei ^a   Wang, Bin ^a   Shi, Yian ^a  

^a Department of Environmental and Radiological Health Sciences   (United States)

Author keywords

Asymmetric synthesis; Chirality; Cyclopentanones; Epoxidation; Rearrangement

Indexed keywords

ASYMMETRIC SYNTHESIS; CHIRALITY; CYCLOPENTANONES; EPOXIDATION; REARRANGEMENT;

ACIDS; CATALYST SELECTIVITY; CATALYSTS; GLUCOSE; KETONES; OXIDATION;

STEREOCHEMISTRY;

CYCLOPENTANE DERIVATIVE; CYCLOPENTANONE; EPOXIDE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; OXIDATION REDUCTION REACTION; STEREOISOMERISM; SYNTHESIS;

CYCLOPENTANES; EPOXY COMPOUNDS; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; STEREOISOMERISM;

EID: 33745289112     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200501520     Document Type: Article

References (61)

1. a) J. Ahman, J. P. Wolfe, M. V. Troutman, M. Palucki, S. L. Buchwald, J. Am. Chem. Soc. 1998, 120, 1918;
2. b) T. Hamada, A. Chieffi, J. Ahman, S. L. Buchwald, J. Am. Chem. Soc. 2002, 124, 1261.
3. B. M. Trost, G. M. Schroeder, J. Kristensen, Angew. Chem. 2002, 114, 3642;
4. Angew. Chem. Int. Ed. 2002, 41, 3492.
5. P. Nilsson, M. Larhed, A. Hallberg, J. Am. Chem. Soc. 2003, 125, 3430.
6. For the catalytic asymmetric phase-transfer alkylation of 2-phenyl-1-indanone, see: U.-H. Dolling, P. Davis, E. J. J. Grabowski, J. Am. Chem. Soc. 1984, 106, 446.
7. For examples of enzymatic resolution approach, see: a) S. Takano, K. Inomata, T. Sato, M. Takahashi, K. Ogasawara, J. Chem. Soc. Chem. Commun. 1990, 290;
8. b) K. Tanaka, T. Taniguchi, K. Ogasawara, Tetrahedron Lett. 2001, 42, 1049.
9. For examples of the rearrangement of aryl substituted 2,3-epoxy acylates and sulfonates, see: a) Y. Kita, A. Furukawa, J. Futamura, K. Higuchi, K. Ueda, H. Fujioka, Tetrahedron Lett. 2000, 41, 2133;
10. b) Y. Kita, A. Furukawa, J. Futamura, K. Ueda, Y. Sawama, H. Hamamoto, H. Fujioka, J. Org. Chem. 2001, 66, 8779;
11. c) Y. Kita, J. Futamura, Y. Ohba, Y. Sawama, J. K. Ganesh, H. Fujioka, J. Org. Chem. 2003, 68, 5917.
12. For the asymmetric protonation of enol derivatives, see: a) K. Ishihara, M. Kaneeda, H. Yamamoto, J. Am. Chem. Soc. 1994, 116, 11 179;
13. b) K. Ishihara, S. Nakamura, M. Kaneeda, H. Yamamoto, J. Am. Chem. Soc. 1996, 118, 12 854;
14. c) A. Yanagisawa, H. Inanami, H. Yamamoto, Chem. Commun. 1998, 1573;
15. d) S. Nakamura, M. Kaneeda, K. Ishihara, H. Yamamoto, J. Am. Chem. Soc. 2000, 122, 8120;
16. e) K. Ishihara, D. Nakashima, Y. Hiraiwa, H. Yamamoto, J. Am. Chem. Soc. 2003, 125, 24.
17. For reviews on acid-promoted epoxide rearrangements, see: a) G. Magnusson, Org. Prep. Proced. Int. 1990, 22, 547;
18. b) B. Rickborn in Comprehensive Organic Synthesis, Vol. 3 (Eds.: B. M. Trost, I. Fleming), Pergamon, Oxford, 1991, p. 733;
19. c) H. Fujioka, Y. Yoshida, Y. Kita, Yuki Gosei Kagaku Kyokaishi 2003, 61, 133.
20. For the rearrangement of oxaspiropentanes and oxaspirohexanes, see: a) B. M. Trost, M. J. Bogdanowicz, J. Am. Chem. Soc. 1972, 94, 4777;
21. b) B. M. Trost, M. J. Bogdanowicz, J. Am. Chem. Soc. 1973, 95, 5321;
22. c) B. M. Trost, P. H. Scudder, J. Am. Chem. Soc. 1977, 99, 7601;
23. d) J. K. Crandall, W. W. Conover, J. Org. Chem. 1978, 43, 3533.
24. For the asymmetric epoxidation of cyclopropylideneethanol and subsequent rearrangement, see: a) H. Nemoto, H. Ishibashi, M. Nagamochi, K. Fukumoto, J. Org. Chem. 1992, 57, 1707;
25. b) H. Nemoto, M. Nagamochi, H. Ishibashi, K. Fukumoto, J. Org. Chem. 1994, 59, 74;
26. c) H. Nemoto, T. Tanabe, K. Fukumoto, J. Org. Chem. 1995, 60, 6785;
27. d) H. Nemoto, K. Fukumoto, Synlett 1997, 863.
28. For asymmetric epoxidations of unfunctionalized cyclopropylidene derivatives and subsequent rearrangement, see: a) M. Yoshida, M. A.-H. Ismail, H. Nemoto, M. Ihara, Heterocycles 1999, 50, 673;
29. b) H. Nemoto, M. Yoshida, K. Fukumoto, M. Ihara, Tetrahedron Lett. 1999, 40, 907;
30. c) M. Yoshida, M. A.-H. Ismail, H. Nemoto, M. Ihara, J. Chem. Soc. Perkin Trans. 1 2000, 2629.
31. For asymmetric dihydroxylations of cyclopropylidene derivatives and subsequent rearrangements, see: a) A. Krief, A. Ronvaux, A. Tuch, Bull. Soc. Chim. Belg. 1997, 106, 699;
32. b) A. Krief, A. Ronvaux, A. Tuch, Tetrahedron 1998, 54, 6903;
33. c) H. Nemoto, J. Miyata, H. Hakamata, K. Fukumoto, Tetrahedron Lett. 1995, 36, 1055;
34. d) H. Nemoto, J. Miyata, H. Hakamata, M. Nagamochi, K. Fukumoto, Tetrahedron 1995, 51, 5511;
35. e) J. M. Diffendal, J. Filan, P. G. Spoors, Tetrahedron Lett. 1999, 40, 6137;
36. f) J. Miyata, H. Nemoto, M. Ihara, J. Org. Chem. 2000, 65, 504.
37. a) Z.-X. Wang, Y. Tu, M. Frohn, J.-R. Zhang, Y. Shi, J. Am. Chem. Soc. 1997, 119, 11224;
38. b) Y. Shi, Acc. Chem. Res. 2004, 37, 488, and references therein.
39. a) H. Tian, X. She, L. Shu, H. Yu, Y. Shi, J. Am. Chem. Soc. 2000, 122, 11 551;
40. b) H. Tian, X. She, H. Yu, L. Shu, Y. Shi, J. Org. Chem. 2002, 67, 2435;
41. c) L. Shu, P. Wang, Y. Gan, Y. Shi, Org. Lett. 2003, 5, 293;
42. d) L. Shu, Y. Shi, Tetrahedron Lett. 2004, 45, 8115.
43. Some epoxides underwent rearrangement on silica gel, thus they were used directly without purification; these epoxides were clean as judged by analysis with NMR spectroscopy and GC analysis (see the Supporting Information).
44. It was found that α-aryl cyclopentanones readily underwent racemization on silica gel; the ketone products were not purified by column chromatography on silica gel and were clean as judged by NMR spectroscopy.
45. For examples of LiI- and LiBr-mediated rearrangements of oxaspiropentanes and oxaspirohexanes, see: a) J. R. Salaun, J. M. Conia, J. Chem. Soc. Chem. Commun. 1971, 1579;
46. b) P. Leriverend, M.-L. Leriverend, C. R. Hebd. Seances Acad. Sci. Ser. C 1975, 280, 791;
47. c) D. H. Aue, M. J. Meshishnek, D. F. Shellhamer, Tetrahedron Lett. 1973, 4799;
48. d) B. M. Trost, L. H. Latimer, J. Org. Chem. 1978, 43, 1031;
49. e) D. R. Morton, Jr., F. C. Brokaw, J. Org. Chem. 1979, 44, 2880;
50. f) F. Huet, A. Lechevallier, J.-M. Conia, Chem. Lett. 1981, 1515;
51. g) S. Halazy, A. Krief, J. Chem. Soc. Chem. Commun. 1982, 1200;
52. h) Y. Tobe, T. Yamashita, K. Kakiuchi, Y. Odaira, J. Chem. Soc. Chem. Commun. 1985, 888;
53. i) T. W. Hart, M.-T. Comte, Tetrahedron Lett. 1985, 26, 2713;
54. j) M. C. Pirrung, S. A. Thomson, J. Org. Chem. 1988, 53, 227;
55. k) T. Chevtchouk, J. Ollivier, J. Salaun, Tetrahedron: Asymmetry 1997, 8, 1011;
56. l) F. Mahuteau-Betzer, L. Ghosez, Tetrahedron Lett. 1999, 40, 5183;
57. m) A. M. Bernard, C. Floris, A. Frongia, P. P. Piras, Synlett 2002, 796.
58. T. B. Freedman, X. Cao, R. K. Dukor, L. A. Nafie, Chirality 2003, 15, 743.
59. 2 was added.
60. R. Downham, P. J. Edwards, D. A. Entwistle, A. B. Hughes, K. S. Kim, S. V. Ley, Tetrahedron: Asymmetry 1995, 6, 2403.
61. Experimental procedures for the asymmetric epoxidation and epoxide rearrangement, the characterization of the epoxides and cyclopentanones, the determination of the ee values of the epoxides and cyclopentanones, and the VCD spectra are given in the Supporting Information.