Intramolecular Carbon-Carbon Bond Forming Reactions Mediated by XTi(OPr-i)3 (X = Cl or OPr-i) / 2i-PrMgBr Reagent: Efficient Synthesis of Cyclopentanols Having an Ethenylidene or Alkynyl Moiety at the β-Position

Synlett

Volumn 1996, Issue 5, 1996, Pages 437-438

  Yoshida, Yukio ^a   Nakagawa, Takashi ^a   Sato, Fumie ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000276782     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-5459     Document Type: Article

References (19)

1. Kočovský, P.; Grech, J. M.; Mitchell, W. L. J. Org. Chem. 1995, 60, 1482 and references cited therein.
2. Sidduri, A.; Rozema, M. J.; Knochel, P. J. Org. Chem. 1993, 58, 2694.
3. Aurrecoechea, J. M.; Antón, R. F. -S. J. Org. Chem. 1994, 59, 702.
4. Jin, J.; Smith, D. T.; Weinreb, S. M. J. Org. Chem. 1995, 60, 5366.
5. For other synthetic methods for preparing 1 or 2 which are not based on intramolecular cyclization reactions, see: a) Johnson, C. R.; Dhanoa, D. S. J. Org. Chem. 1987, 52, 1885. b) Alexakis, A.; Marek, I.; Mangeney, P.; Normant, J. F. Tetrahedron 1991, 47, 1677. c) Garratt, P. J. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I., Eds.; Pergamon Press: New York, 1991; Vol 3; p 277. d) Yamaguchi, M. ibid. 1991; Vol.1; p 342.
6. For other synthetic methods for preparing 1 or 2 which are not based on intramolecular cyclization reactions, see: a) Johnson, C. R.; Dhanoa, D. S. J. Org. Chem. 1987, 52, 1885. b) Alexakis, A.; Marek, I.; Mangeney, P.; Normant, J. F. Tetrahedron 1991, 47, 1677. c) Garratt, P. J. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I., Eds.; Pergamon Press: New York, 1991; Vol 3; p 277. d) Yamaguchi, M. ibid. 1991; Vol.1; p 342.
7. For other synthetic methods for preparing 1 or 2 which are not based on intramolecular cyclization reactions, see: a) Johnson, C. R.; Dhanoa, D. S. J. Org. Chem. 1987, 52, 1885. b) Alexakis, A.; Marek, I.; Mangeney, P.; Normant, J. F. Tetrahedron 1991, 47, 1677. c) Garratt, P. J. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I., Eds.; Pergamon Press: New York, 1991; Vol 3; p 277. d) Yamaguchi, M. ibid. 1991; Vol.1; p 342.
8. For other synthetic methods for preparing 1 or 2 which are not based on intramolecular cyclization reactions, see: a) Johnson, C. R.; Dhanoa, D. S. J. Org. Chem. 1987, 52, 1885. b) Alexakis, A.; Marek, I.; Mangeney, P.; Normant, J. F. Tetrahedron 1991, 47, 1677. c) Garratt, P. J. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I., Eds.; Pergamon Press: New York, 1991; Vol 3; p 277. d) Yamaguchi, M. ibid. 1991; Vol.1; p 342.
9. a) Kasatkin, A.; Nakagawa, T.; Okamoto, S.; Sato, F. J. Am. Chem. Soc. 1995, 117, 3881.
10. b) Harada, K.; Urabe, H.; Sato, F. Tetrahedron Lett. 1995, 36, 3203.
11. c) Nakagawa, T.; Kasatkin, A.; Sato, F. ibid. 1995, 36, 3207.
12. d) Urabe, H.; Hata, T. Sato, F. ibid. 1995, 36, 4261.
13. e) Gao, Y.; Harada, K.; Sato, F. ibid. 1995, 36, 5913.
14. f) Kasatkin, A.; Sato, F.; Okamoto, S. ibid. 1995, 36, 6075.
15. g) Kasatkin, A.; Sato, F. ibid. 1995, 36, 6079.
16. Furuta, K.; Ishiguro, M.; Haruta, R.; Ikeda, N.; Yamamoto, H.; Bull. Chem. Soc. Jpn. 1984, 57, 2768.
17. 3) δ 17.2, 18.5, 23.5, 31.0, 34.5, 36.0, 78.5, 85.2, 110.3, 201.9
18. 2Zr-mediated reaction.
19. 3) δ 14.0, 18.7, 20.4, 22.5, 25.0, 28.5, 29.1, 31.3, 31.8, 37.7, 44.3, 80.2, 82.9, 84.7