Skip to main content
SpringerLink
Log in

Metal homoenolates from siloxycyclopropanes

  • Conference paper
  • First Online:
Book cover Small Ring Compounds in Organic Synthesis IV

Part of the book series: Topics in Current Chemistry ((TOPCURRCHEM,volume 155))

Abstract

The potential of metal homoenolates as multifunctional reagents in organic synthesis has become recognized in the last decade. Ring opening of siloxycyclopropanes by Lewis acidic metals currently provides the best route to the metal homoenolates, which are either isolable as a stable complex or exist only as a transient organometallic species. This review summarizes, for the first time, the research activities of metal homoenolate chemistry. Other synthetically useful routes to metal homoenolates are also described.

This is a preview of subscription content, log in via an institution to check access.

Access this chapter

Log in via an institution

Institutional subscriptions

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

8 References

  1. Nickon A, Lambert JL (1962) J. Am. Chem. Soc. 84: 4604

    Google Scholar 

  2. Werstiuk NH (1983) Tetrahedron 39: 205; Ryu I, Sonoda N. (1985) J. Syn. Org. Chem., Jpn. 43: 112; Nakamura E (1989) J. Syn. Org. Chem. Jpn. 47: 931

    Google Scholar 

  3. Seebach D (1979) Angew. Chem. Int. Ed. Engl. 18: 239; Evans DA, Andrews GC (1974) Acc. Chem. Res. 7: 147

    Google Scholar 

  4. Brewis S, Hughes PR: J. Chem. Soc., Chem. Commun. 1967: 71

    Google Scholar 

  5. Bennett MA, Watt R: J. Chem. Soc., Chem. Commun. 1971: 95; Bennett MA, Robertson GB, Watt R, Whimp PO: J. Chem. Soc., Chem. Commun 1971: 752

    Google Scholar 

  6. Hoppe D (1984) Angew. Chem. Int. Ed. Engl. 23: 932; see also ref. 8 in Ref. 10

    Google Scholar 

  7. DeBoey A, DePuy CH (1970) J. Am. Chem. Soc. 92: 4008; Gibson DH, DePuy CH (1974) Chem. Rev. 74: 605

    Google Scholar 

  8. Ryu I, Matsumoto K, Ando M, Murai S, Sonoda N (1980) Tetrahedron Lett. 21: 4283

    Google Scholar 

  9. Nakamura E, Kuwajima I (1977) J. Am. Chem. Soc. 99: 7360

    Google Scholar 

  10. Nakamura E, Kuwajima I (1983) J. Am. Chem. Soc. 105: 651

    Google Scholar 

  11. Nakamura E, Shimada J, Kuwajima I (1985) Organometallics 4: 641

    Google Scholar 

  12. Denis JM, Conia JM: Tetrahedron Lett. 1972: 4593, Conia JM, Girard C: Tetrahedron Lett. 1973: 2767: Girard C, Conia JM: Tetrahedron Lett. 1974: 3327

    Google Scholar 

  13. le Goaller R, Pierre JL: Bull. Chim. Soc. Fr. 1973: 153

    Google Scholar 

  14. Rubottom GM, Lopez MI (1973) J. Org. Chem. 38: 2097

    Google Scholar 

  15. Murai S, Aya T, Sonoda N (1973) J. Org. Chem. 38: 4354

    Google Scholar 

  16. Rousseaux G, Slougui N (1983) Tetrahedron Lett. 24: 1251

    Google Scholar 

  17. Furukawa J, Kawabata N, Nishimura J: Tetrahedron Lett. 1966: 3353

    Google Scholar 

  18. Miyano S, Izumi Y, Fujii H, Hashimoto H: Synthesis 1977: 700

    Google Scholar 

  19. Nakamura E, Oshino H, Kuwajima I (1986) J. Am. Chem. Soc. 108: 3745

    Google Scholar 

  20. Ito Y, Saegusa T (1977) J. Org. Chem. 42: 2326

    Google Scholar 

  21. Rühlmann K: Synthesis 1971: 236; Saläun J, Marguerite J. (1985) Org. Synth. 63: 147

    Google Scholar 

  22. Saläun J (1983) Chem. Rev. 83: 619

    Google Scholar 

  23. Nakamura E, Sekiya K, Kuwajima I (1987) Tetrahedron Lett. 28: 337

    Google Scholar 

  24. Tamaru Y et al. (1987) 54th Annual Meeting of the Chemical Society of Japan, Tokyo, 1987; 3IIIM32.

    Google Scholar 

  25. Wailes PC, Coutts RSP, Weigold H (1974) Organometallic chemistry of titanium, zirconium, and hafnium, chap 2 Academic, New York

    Google Scholar 

  26. Murai S, Aya T, Renge T, Ryu I, Sonoda N (1974) J. Org. Chem. 39: 858; Ryu I, Murai S, Otani S, Sonoda N: Tetrahedron Lett. 1977: 1995

    Google Scholar 

  27. Oshino H. (1984) Master's thesis submitted to Tokyo Institute Technology

    Google Scholar 

  28. Nakamura E, Kuwajima I (1984) J. Am. Chem. Soc. 106: 3368; Nakamura E, Kuwajima I (1988) Org. Synth. 66: 43

    Google Scholar 

  29. Nakamura E, Aoki S, Sekiya K, Oshino H, Kuwajima I (1987) J. Am. Chem. Soc. 109: 8056

    Google Scholar 

  30. Harrison PG, King TJ, Healy MA (1979) J. Organomet. Chem. 182: 17

    Google Scholar 

  31. Ryu I, Murai S, Sonoda N (1986) J. Org. Chem. 51: 2389

    Google Scholar 

  32. Jorgensen JJ (1970) Organic Reactions 18: 1; Negishi E, Bagheri V, Chatterjee S, Luo F-T, Miller JA, Stoll AT (1983) Tetrahedron Lett. 24: 5181

    Google Scholar 

  33. Oshino H, Nakamura E, Kuwajima I (1985) J. Org. Chem. 50: 2802

    Google Scholar 

  34. Ryu I, Rhee I, Ryang M, Omura H, Murai S, Sonoda N (1984) Synthetic Commun. 14: 1174

    Google Scholar 

  35. Reetz M (1986) Organotitanium reagents in organic synthesis, Springer, Berlin Heidelberg New York

    Google Scholar 

  36. Boersma J (1982) In: Wilkinson G (ed) Comphrensive organometallic chemistry Pergamon, Oxford p 823

    Google Scholar 

  37. Giese B, Horler H, Zwick W (1982) Tetrahedron Lett. 23: 931; Giese B, Horler H (1983) Tetrahedron Lett. 24: 3221

    Google Scholar 

  38. Corey EJ, Boaz NW (1985) Tetrahedron Lett. 26: 6015, 6019; Alexakis A, Berlan J, Besace Y (1986) Tetrahedron Lett. 27: 1047; Horiguchi Y, Matsuzawa S, Nakamura E, Kuwajima I (1986) Tetrahedron Lett. 27: 4025; Nakamura E, Matsuzawa S, Horiguchi Y, Kuwajima I (1986) Tetrahedron Lett. 27: 4029; Johnson CR, Marren TJ (1987) Tetrahedron Lett. 28: 27

    Google Scholar 

  39. Horiguchi Y, Nakamura E, Kuwajima I (1986) J. Org. Chem. 51: 4323

    Google Scholar 

  40. Nakamura E, Kuwajima I (1986) Tetrahedron Lett. 27: 83

    Google Scholar 

  41. Stang PJ, Hanack M, Subramanian LR: Synthesis, 1982: 85

    Google Scholar 

  42. Caine D, Frobese AS: Tetrahedron Lett. 1978: 883

    Google Scholar 

  43. Goswami R, Corcoran DE (1982) Tetrahedron Lett. 23: 1463

    Google Scholar 

  44. Goswami R, Corcoran DE (1983) J. Am. Chem. Soc. 105: 7182

    Google Scholar 

  45. Goswami R (1985) J. Org. Chem. 50: 5907

    Google Scholar 

  46. Sano H, Tanaka Y, Migita T: 50th Annual Meeting of the Chemical Society of Japan, Tokyo, 1985; 2V02

    Google Scholar 

  47. Sano H., Suzuki T, Migita T: 50th Annual Meeting of the Chemical Society of Japan, Tokyo, 1985; 2V03

    Google Scholar 

  48. Nishiyama H, Matsumoto M, Matsukura T, Miura R, Itoh K (1985) Organometallics 4: 1911

    Google Scholar 

  49. Tamaru Y, Ochiai H, Nakamura T, Tsubaki K, Yoshida Z (1985) Tetrahedron Lett. 26: 5559; Tamaru Y, Ochiai H, Nakamura T, Yoshida Z (1986) Tetrahedron Lett. 27: 955

    Google Scholar 

  50. Ito Y, Fujii S, Saegusa T (1976) J. Org. Chem. 41: 2073; Ito Y, Sugaya T, Nakatsuka M, Saegusa T (1977) J. Am. Chem. Soc. 99: 8366; Ito Y, Fujii S, Nakatsuka M, Kawamoto F, Saegusa T (1988) Org. Synth. Coll. Vol. 6: 327

    Google Scholar 

  51. Ryu I, Ando M, Ogawa A, Murai S, Sonoda N (1983) J. Am. Chem. Soc. 105: 7192

    Google Scholar 

  52. Stork G, Davies JE, Meisels A (1963) J. Am. Chem. Soc. 85: 3419

    Google Scholar 

  53. Ryu I, Ogawa A, Sonoda N: J. Chem. Soc., Jpn. 1985: 442

    Google Scholar 

  54. Ryu I, Kameyama Y, Matsumoto K, Murai S, Sonoda N (Unpublished work cited in Ref. [2])

    Google Scholar 

  55. Ryu I, Suzuki H, Ogawa A, Kambe N, Sonoda N (1988) Tetrahedton Lett. 29: 6137

    Google Scholar 

  56. Aoki S (unpublished results at Tokyo Institute of Technology)

    Google Scholar 

  57. Aoki S, Fujimura T, Nakamura E, Kuwajima I (1988) J. Am. Chem. Soc. 110: 3296; Aoki S, Nakamura E, Kuwajima I (1988) Tetrahedron Lett. 29: 1541

    Google Scholar 

  58. Rousseaux G, Sloughui N (1984) J. Am. Chem. Soc. 106: 7283

    Google Scholar 

  59. Rubottom GM, Marrero R, Krueger DS, Schreiner JL: Tetrahedron Lett. 1977: 4013

    Google Scholar 

  60. Rubottom GM, Beedle EC, Kim CW, Mott RC (1985) J. Am. Chem. Soc. 107: 4230

    Google Scholar 

  61. Bishop KC III (1976) Chem. Rev. 76: 461

    Google Scholar 

  62. Mann BE, Taylor BF (1981) 13C NMR Data for Organometallic Compounds, Academic, London

    Google Scholar 

  63. Nakamura E, Kuwajima I (1985) J. Am. Chem. Soc. 107: 2138

    Google Scholar 

  64. Carmely S, Kashman Y (1981) Tetrahedron 37: 2397

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Department of Chemistry, Tokyo Institute of Technology, 152, Meguro, Tokyo, Japan

    Isao Kuwajima & Eiichi Nakamura

Authors
  1. Isao Kuwajima
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Eiichi Nakamura
    View author publications

    You can also search for this author in PubMed Google Scholar

Editor information

Armin deMeijere

Rights and permissions

Reprints and permissions

Copyright information

© 1990 Springer-Verlag

About this paper

Cite this paper

Kuwajima, I., Nakamura, E. (1990). Metal homoenolates from siloxycyclopropanes. In: deMeijere, A. (eds) Small Ring Compounds in Organic Synthesis IV. Topics in Current Chemistry, vol 155. Springer, Berlin, Heidelberg. https://doi.org/10.1007/3-540-52422-3_1

Download citation

  • DOI: https://doi.org/10.1007/3-540-52422-3_1

  • Published:

  • Publisher Name: Springer, Berlin, Heidelberg

  • Print ISBN: 978-3-540-52422-9

  • Online ISBN: 978-3-540-46984-1

  • eBook Packages: Springer Book Archive

Publish with us

Policies and ethics

Search

Navigation