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Main, C.A.; Rahman, S.S.; Hartley, R.C. (2008)
Publisher: Elsevier
Languages: English
Types: Article
Subjects: QD
Alkylidenation of lactones with functionalised titanium carbenoid reagents (Schrock carbenes) followed by acid-induced cyclisation of the resulting enol ethers constitutes a new method for the preparation of [4.4], [4.5] and [5.5] spiroacetals (1,6-dioxaspiro[4.4]nonanes, 1,6-dioxaspiro[4.5]decanes and 1,7-dioxaspiro[5.5]undecanes, respectively, sometimes termed 5,5-, 5,6- and 6,6-spiroketals). The titanium carbenoids are easily generated from readily available thioacetals.
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    • 1. Reviews: (a) Mead, K. T.; Brewer, B. N. Curr. Org. Chem. 2003, 7, 227-256. (b) Aho, J. E.; Pihko, P. M.; Rissa, T. K. Chem. Rev. 2005, 105, 4406-4440. (c) Perron, F.; Albizati, K. F. Chem. Rev. 1989, 89, 1617-1661.
    • 2. Recent examples include: (a) Keaton, K. A.; Phillips, A. J. Org. Lett. 2007, 9, 2717- 2719. (b) Tsang, K. Y.; Brimble, M. A. Tetrahedron 2007, 63, 6015-6034. (c) Lu, C.- D.; Zakarian, A. Org. Lett. 2007, 9, 3161-3163. (c) Velluci, D.; Rychnovsky, S. D. Org. Lett. 2007, 9, 711-714. (e) Denmark, S. E.; Regens, C. S.; Kobayashi, T. J. Am. Chem. Soc. 2007, 129, 2774-2776. (f) Phillips, S. T.; Shair, M. D. J. Am. Chem. Soc. 2007, 129, 6589-6598. (g) Lowe, J. T.; Wrona, I. E.; Panek, J. S. Org. Lett. 2007, 9, 327-330.
    • 3. Hayes, P.; Maignan, C. Synthesis 1999, 783-786.
    • 4. Tietze, L. F.; Schneider, G.; Wölfling, J.; Fecher, A.; Nöbel, T.; Peterson, S.; Schuberth, I.; Wulff, C. Chem. Eur. J. 2000, 6, 3755-3760.
    • 5. Zhou, G.; Zheng, D.; Da, S.; Xie, Z.; Li, Y. Tetrahedron Lett. 2006, 47, 3349-3352.
    • 6. Cuzzupe, A. N.; Hutton, C. A.; Lilly, M. J.; Mann, R. K.; McRae, K. J.; Zammit, S. C.; Rizzacasa, M. A. J. Org. Chem. 2001, 66, 2382-2393.
    • 7. Ireland, R. E.; Thaisrivongs, S.; Dussault, P. H. J. Am. Chem. Soc. 1988, 110, 5768- 5779.
    • 8. Chang, C.-F.; Yang, W.-B.; Chang, C.-C.; Lin, C.-H. Tetrahedron Lett. 2002, 43, 6515-6519.
    • 9. Paterson, D. E.; Griffin, F. K.; Alcaraz, M.-L.; Taylor, R. J. K. Eur. J. Org. Chem. 2002, 1323-1336.
    • 10. Ousset, J. B.; Mioskowski, C.; Yang, Y.-L.; Falck, J. R. Tetrahedron Lett. 1984, 25, 5903-5906.
    • 11. Godoy, J.; Ley, S. V.; Lygo, B. J. Chem. Soc., Chem. Commun. 1984, 1381-1382.
    • 12. Wang, C.; Forsyth, C. J. Org. Lett. 2006, 8, 2997-3000.
    • 13. Evans, D. A.; Rajapakse, H. A.; Stenkamp, D. Angew. Chem. Int. Ed. 2002, 41, 4569-4573.
    • 14. Yang, W.-B.; Yang, Y.-Y.; Gu, Y.-F., Wang, S.-H.; Chang, C.-C.; Lin, C.-H. J. Org. Chem. 2002, 67, 3773-3782.
    • 15. Tebbe, F. N.; Parshall, G. W.; Reddy, G. S. J. Am. Chem. Soc. 1978, 100, 3611- 3613.
    • 16. Petasis, N. A.; Bzowej, E. I. J. Am. Chem. Soc. 1990, 112, 6392-6394.
    • 17. Yan, T.-H.; Chien, C.-T.; Tsai, C.-C.; Lin, K.-W.; Wu, Y.-H. Org. Lett. 2004, 6, 4965-4967.
    • 18. For a review of titanium carbenoids see: Hartley, R. C.; Li, J.; Main, C. A.; McKiernan, G. J. Tetrahedron 2007, 63, 4825-4864.
    • 19. Mortimore, M.; Kocienski, P. Tetrahedron Lett. 1988, 29, 3357-3360.
    • 20. Takai, K.; Kataoka, Y.; Miyai, J.; Okazoe, T.; Oshima, K.; Utimoto, K. Org. Synth. 1996, 73, 73-84.
    • 21. There are now good routes to 1,1-dibromoalkanes: (a) Takeda, T.; Sasaki, R.; Yamauchi, S.; Fujiwara, T. Tetrahedron 1997, 53, 557-566. (b) Furrow, M. E.; Myers, A. G. J. Am. Chem. Soc. 2004, 126, 5436-5445.
    • 22. Recent examples include: (a) Boxer, M. B.; Yamamoto, H. J. Am. Chem. Soc. 2007, 129, 2762-2763. (b) Canova, S.; Bellosta, V.; Bigot, A.; Mailliet, P.; Mignani, S.; Cossy, J. Org. Lett. 2007, 9, 145-148. (c) Sakaguchi, H.; Tokuyama, H.; Fukuyama, T. Org. Lett. 2007, 9, 1635-1638. (d) Inoue, M.; Nakada, M. J. Am. Chem. Soc. 2007, 129, 4164-4165. (e) Paquette, L. A.; Parker, G. D.; Tei, T.; Dong, S. J. Org. Chem. 2007, 72, 7125-7134. (f) D'Annibale, A.; Ciaralli, L.; Bassetti, M.; Pasquini, C. J. Org. Chem. 2007, 72, 6067-6074. (g) Enders, D.; Dhulut, S.; Steinbusch, D.; Herrbach, A. Chem. Eur. J. 2007, 13, 3942-2949. (h) Van Orden, L. J.; Patterson, B. D.; Rychnovsky, S. D. J. Org. Chem. 2007, 72, 5784-5793. (i) Nakashima, K.; Kikuchi, N.; Shirayama, D.; Miki, T.; Ando, K.; Sono, M.; Suzuki, S.; Kawase, M.; Kondoh, M.; Sato, M.; Tori, M. Bull. Chem. Soc. Jpn. 2007, 80, 387-394. (j) Krishna, P. R.; Reddy, P. S. Tetrahedron 2007, 63, 3995-3999. (k) Alcaide, B.; Almendros, P.; del Campo, T. M.; RodríguezAcebes, R. Adv. Synth. Catal. 2007, 349, 749-758.
    • 23. Recent examples include: (a) Kumar, I.; Rode, C. V. Tetrahedron: Asymmetry 2007, 18, 1975-1980. (b) Vuagnoux-D'Augustin, M.; Kehrli, S.; Alexakis, A. Synlett 2007, 2057-2060.
    • 24. Recent examples include: (a) Morimoto, N.; Ogino, N.; Narita, T.; Kitamura, S.; Akiyoshi, K. J. Am. Chem. Soc. 2007, 129, 458-459 (supporting information). (b) ElBadri, M. H.; Willenbring, D.; Tantillo, D. J.; Gervay-Hague, J. J. Org. Chem. 2007, 72, 4663-4672.
    • 25. Horikawa, Y.; Watanabe, M.; Fujiwara, T.; Takeda, T. J. Am. Chem. Soc. 1997, 119, 1127-1128.
    • 26. Macleod, C.; McKiernan, G. J.; Guthrie, E. J.; Farrugia, L. J.; Hamprecht, D. W.; Macritchie, J.; Hartley, R. C. J. Org. Chem. 2003, 68, 387-401.
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