Synthesis, including asymmetric synthesis, of 1-substituted cyclopentenes from cyclobutanones with one-carbon ring-expansion by 1,2-carbon-carbon insertion of magnesium carbenoids

Tetrahedron

Volumn 67, Issue 6, 2011, Pages 1102-1113

  Satoh, Tsuyoshi ^a   Awata, Yu ^a   Kato, Yuichi ^a   Ogata, Shingo ^a   Ishigaki, Masashi ^a   Sugiyama, Shimpei ^a   Saitoh, Hideki ^a  

^a TOKYO UNIVERSITY OF SCIENCE   (Japan)

Author keywords

1,2 Carbon carbon insertion; Cyclopentene; Magnesium carbenoid; One carbon ring expansion; Rearrangement

Indexed keywords

ACETONITRILE; AMIDE; CARBENOID; CARBON; CYCLOBUTANONE DERIVATIVE; CYCLOPENTENE DERIVATIVE; GRIGNARD REAGENT; LITHIUM; MAGNESIUM; SULFOXIDE; VINYL DERIVATIVE;

ARTICLE; ASYMMETRIC SYNTHESIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; OPTICS; PRIORITY JOURNAL; QUANTITATIVE ANALYSIS; QUANTUM YIELD; REACTION ANALYSIS; STEREOSPECIFICITY;

EID: 78751569571     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2010.12.023     Document Type: Article

References (46)

1. Some selected reviews for the ring enlargement reactions:
2. T. Hiyama, and H. Nozaki J. Syn. Org. Chem. Jpn. 35 1977 979
3. G.R. Krow Tetrahedron 43 1987 3
4. M. Hesse Ring Enlargement in Organic Chemistry 1991 VHC Weinheim
5. C.J. Roxburg Tetrahedron 49 1993 10749
6. P. Dowd, and W. Zhang Chem. Rev. 93 1993 2091
7. W. Tochtermann, and P. Kraft Synlett 1996 1029
8. T. Satoh J. Syn. Org. Chem. Jpn. 67 2009 381
9. J. Villieras, C. Bacquet, and J.F. Normant Organomet. Chem. 40 1972 C1
10. J. Villieras, C. Bacquet, D. Masure, and J.F. Normant Organomet. Chem. 50 1973 C7
11. G. Kobrich, and J. Grosser Tetrahedron Lett. 13 1972 4117
12. G. Kobrich, and J. Grosser Chem. Ber. 106 1973 2626
13. H. Taguchi, H. Yamamoto, and H. Nozaki Tetrahedron Lett. 13 1972 4661
14. H. Taguchi, H. Yamamoto, and H. Nozaki J. Am. Chem. Soc. 96 1974 6510
15. H. Taguchi, H. Yamamoto, and H. Nozaki Tetrahedron Lett. 17 1976 2617
16. H. Taguchi, H. Yamamoto, and H. Nozaki Bull. Chem. Soc. Jpn. 50 1977 1592
17. T. Hiyama, M. Shinoda, and H. Nozaki Tetrahedron Lett. 20 1979 3529
18. W.D. Abraham, M. Bhupathy, and T. Cohen Tetrahedron Lett. 28 1987 2203
19. T. Satoh, and K. Miyashita Tetrahedron Lett. 45 2004 4859
20. K. Miyashita, and T. Satoh Tetrahedron 61 2005 5067
21. T. Satoh, S. Tanaka, and N. Asakawa Tetrahedron Lett. 47 2006 6769
22. S. Tanaka, T. Anai, M. Tadokoro, and T. Satoh Tetrahedron 64 2008 7199
23. T. Satoh Chem. Soc. Rev. 36 2007 1561
24. T. Satoh Z. Rappoport, I. Marek, The Chemistry of Organomagnesium Compounds 2008 John Wiley Chichester,UK 717 769
25. T. Satoh, S. Ogata, and D. Wakasugi Tetrahedron Lett. 47 2006 7249
26. S. Ogata, H. Saitoh, D. Wakasugi, and T. Satoh Tetrahedron 64 2008 5711
27. Preliminary results of this study were reported as a letter: T. Satoh, Y. Awata, S. Ogata, S. Sugiyama, M. Tanaka, and M. Tori Tetrahedron Lett. 50 2009 1961
28. H. Kashima, T. Kawashima, D. Wakasugi, and T. Satoh Tetrahedron 63 2007 3953
29. S. Sugiyama, and T. Satoh Tetrahedron: Asymmetry 16 2005 665
30. A.M. Bernard, A. Frongia, F. Secci, and P.P. Piras Chem. Commun. 2005 3853
31. S. Ogata, S. Masaoka, K. Sakai, and T. Satoh Tetrahedron Lett. 48 2007 5017 The relative stereochemistry of the 2-phenylethyl group was not determined
32. T. Satoh, S. Kobayashi, S. Nakanishi, K. Horiguchi, and S. Irisa Tetrahedron 55 1999 2515
33. R.W. Hoffmann, B. Holzer, O. Knopff, and K. Harms Angew. Chem., Int. Ed. 39 2000 3072
34. T. Satoh, R. Matsue, T. Fujii, and S. Morikawa Tetrahedron 57 2001 3891
35. R.W. Hoffmann Chem. Soc. Rev. 32 2003 225
36. H. Yamashita, and T. Satoh Tetrahedron 65 2009 613
37. M. Kido, S. Sugiyama, and T. Satoh Tetrahedron: Asymmetry 18 2007 1934
38. S. Sugiyama, N. Nakaya, and T. Satoh Tetrahedron: Asymmetry 19 2008 401
39. T. Satoh, T. Oohara, Y. Ueda, and K. Yamakawa J. Org. Chem. 54 1989 3130
40. T. Satoh, Y. Kamide, and S. Sugiyama Tetrahedron 60 2004 11805
41. T. Satoh, and H. Ota Tetrahedron 56 2000 5113
42. D. Wakasugi, and T. Satoh Tetrahedron 61 2005 1245
43. H. Saitoh, and T. Satoh Tetrahedron Lett. 51 2010 3380
44. R.C. Gadwood, I.M. Mallick, and A.J. DeWinter J. Org. Chem. 52 1987 774
45. N. Ono, I. Hamamoto, T. Kawai, A. Kaji, R. Tamura, and M. Kakihana Bull. Chem. Soc. Jpn. 59 1986 405
46. R. Tamura, Y. Kai, M. Kakihana, K. Hayashi, M. Tsuji, T. Nakamura, and D. Oda J. Org. Chem. 51 1986 4375