Preparation of Oxetanes by Zirconium(IV) Chloride Promoted Cycloaddition of Allylsilane to Aldehydes

Synlett

Volumn 1996, Issue 11, 1996, Pages 1095-1096

  Akiyama, Takahiko ^a   Yamanaka, Masahiro ^a  

^a GAKUSHUIN UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001892550     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-5692     Document Type: Article

References (26)

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3. Porco, J. A. Jr.; Schreiber, S. L. In Comprehensive Organic Synthesis; Trost, B. M., Ed., Pergamon Press, Oxford, 1991, Vol. 5, p 151. Bach, T. Tetrahedron Lett. 1994, 35, 5845. Bach, T. Angew. Chem., Int. Ed. Engl. 1996, 35, 884. Bach, T.; Jödicke, K.; Kather, K.; Hecht, J. Angew. Chem., Int. Ed. Engl. 1995, 34, 2271. Bach, T.; Kather, K. Tetrahedron 1994, 50, 12319. Bach, T.; Lange, C. Tetrahedron Lett. 1996, 37, 4363.
4. Porco, J. A. Jr.; Schreiber, S. L. In Comprehensive Organic Synthesis; Trost, B. M., Ed., Pergamon Press, Oxford, 1991, Vol. 5, p 151. Bach, T. Tetrahedron Lett. 1994, 35, 5845. Bach, T. Angew. Chem., Int. Ed. Engl. 1996, 35, 884. Bach, T.; Jödicke, K.; Kather, K.; Hecht, J. Angew. Chem., Int. Ed. Engl. 1995, 34, 2271. Bach, T.; Kather, K. Tetrahedron 1994, 50, 12319. Bach, T.; Lange, C. Tetrahedron Lett. 1996, 37, 4363.
5. Porco, J. A. Jr.; Schreiber, S. L. In Comprehensive Organic Synthesis; Trost, B. M., Ed., Pergamon Press, Oxford, 1991, Vol. 5, p 151. Bach, T. Tetrahedron Lett. 1994, 35, 5845. Bach, T. Angew. Chem., Int. Ed. Engl. 1996, 35, 884. Bach, T.; Jödicke, K.; Kather, K.; Hecht, J. Angew. Chem., Int. Ed. Engl. 1995, 34, 2271. Bach, T.; Kather, K. Tetrahedron 1994, 50, 12319. Bach, T.; Lange, C. Tetrahedron Lett. 1996, 37, 4363.
6. Porco, J. A. Jr.; Schreiber, S. L. In Comprehensive Organic Synthesis; Trost, B. M., Ed., Pergamon Press, Oxford, 1991, Vol. 5, p 151. Bach, T. Tetrahedron Lett. 1994, 35, 5845. Bach, T. Angew. Chem., Int. Ed. Engl. 1996, 35, 884. Bach, T.; Jödicke, K.; Kather, K.; Hecht, J. Angew. Chem., Int. Ed. Engl. 1995, 34, 2271. Bach, T.; Kather, K. Tetrahedron 1994, 50, 12319. Bach, T.; Lange, C. Tetrahedron Lett. 1996, 37, 4363.
7. Porco, J. A. Jr.; Schreiber, S. L. In Comprehensive Organic Synthesis; Trost, B. M., Ed., Pergamon Press, Oxford, 1991, Vol. 5, p 151. Bach, T. Tetrahedron Lett. 1994, 35, 5845. Bach, T. Angew. Chem., Int. Ed. Engl. 1996, 35, 884. Bach, T.; Jödicke, K.; Kather, K.; Hecht, J. Angew. Chem., Int. Ed. Engl. 1995, 34, 2271. Bach, T.; Kather, K. Tetrahedron 1994, 50, 12319. Bach, T.; Lange, C. Tetrahedron Lett. 1996, 37, 4363.
8. Akiyama, T.; Ishikawa, K.; Ozaki, S. Chem. Lett. 1994, 627. Akiyama, T.; Yasusa, T.; Ishikawa, K.; Ozaki, S. Tetrahedron Lett. 1994, 35, 8401.
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10. Akiyama, T.; Kirino, M. Chem. Lett. 1995, 723.
11. 4 as a Lewis acid, see: Maeta, H.; Nagasawa, T.; Handa, Y.; Takei, T.; Osamura, Y.; Suzuki, K. Tetrahedron Lett. 1995, 36, 899. Asao, N.; Liu, J.; Sudoh, T.; Yamamoto, Y. J. Chem. Soc., Chem. Commun. 1995, 2405. Harrowven, D. C.; Dainty, R. F. Tetrahedron Lett. 1996, 37, 3607. Asao, N.; Liu, J.-X.; Sudoh, T.; Yamamoto, Y. J. Org. Chem. 1996, 61, 4568. Asao, N.; Matsukawa, Y.; Yamamoto, Y. J. Chem. Soc., Chem. Commun. 1996, 1513.
12. 4 as a Lewis acid, see: Maeta, H.; Nagasawa, T.; Handa, Y.; Takei, T.; Osamura, Y.; Suzuki, K. Tetrahedron Lett. 1995, 36, 899. Asao, N.; Liu, J.; Sudoh, T.; Yamamoto, Y. J. Chem. Soc., Chem. Commun. 1995, 2405. Harrowven, D. C.; Dainty, R. F. Tetrahedron Lett. 1996, 37, 3607. Asao, N.; Liu, J.-X.; Sudoh, T.; Yamamoto, Y. J. Org. Chem. 1996, 61, 4568. Asao, N.; Matsukawa, Y.; Yamamoto, Y. J. Chem. Soc., Chem. Commun. 1996, 1513.
13. 4 as a Lewis acid, see: Maeta, H.; Nagasawa, T.; Handa, Y.; Takei, T.; Osamura, Y.; Suzuki, K. Tetrahedron Lett. 1995, 36, 899. Asao, N.; Liu, J.; Sudoh, T.; Yamamoto, Y. J. Chem. Soc., Chem. Commun. 1995, 2405. Harrowven, D. C.; Dainty, R. F. Tetrahedron Lett. 1996, 37, 3607. Asao, N.; Liu, J.-X.; Sudoh, T.; Yamamoto, Y. J. Org. Chem. 1996, 61, 4568. Asao, N.; Matsukawa, Y.; Yamamoto, Y. J. Chem. Soc., Chem. Commun. 1996, 1513.
14. 4 as a Lewis acid, see: Maeta, H.; Nagasawa, T.; Handa, Y.; Takei, T.; Osamura, Y.; Suzuki, K. Tetrahedron Lett. 1995, 36, 899. Asao, N.; Liu, J.; Sudoh, T.; Yamamoto, Y. J. Chem. Soc., Chem. Commun. 1995, 2405. Harrowven, D. C.; Dainty, R. F. Tetrahedron Lett. 1996, 37, 3607. Asao, N.; Liu, J.-X.; Sudoh, T.; Yamamoto, Y. J. Org. Chem. 1996, 61, 4568. Asao, N.; Matsukawa, Y.; Yamamoto, Y. J. Chem. Soc., Chem. Commun. 1996, 1513.
15. 4 as a Lewis acid, see: Maeta, H.; Nagasawa, T.; Handa, Y.; Takei, T.; Osamura, Y.; Suzuki, K. Tetrahedron Lett. 1995, 36, 899. Asao, N.; Liu, J.; Sudoh, T.; Yamamoto, Y. J. Chem. Soc., Chem. Commun. 1995, 2405. Harrowven, D. C.; Dainty, R. F. Tetrahedron Lett. 1996, 37, 3607. Asao, N.; Liu, J.-X.; Sudoh, T.; Yamamoto, Y. J. Org. Chem. 1996, 61, 4568. Asao, N.; Matsukawa, Y.; Yamamoto, Y. J. Chem. Soc., Chem. Commun. 1996, 1513.
16. In the case of 3-phenylpropanal and hexanal, use of toluene did not increase the yields of the oxetanes.
17. 2, hexane: ethyl acetate = 15:1, v/v) gave 3f (63 mg, 75%).
18. 3) δ=136.14, 133.33, 133.18, 129.49, 129.44, 127.73, 127.71, 69.91, 66.08, 59.29, 43.68, 27.63, 25.83, 22.47, 18.24, 18.18, and -5.42.
19. Keck, G. E.; Boden, E. P. Tetrahedron Lett. 1984, 25, 265.
20. 12 (Equation Presented)
21. Recently, construction of cyclobutanes by Lewis acid promoted [2+2] cycloaddition of allylsilanes to α,β-unsaturated carbonyl compounds have been reported; Hojo, M.; Tomita, K.; Hirohara, Y.; Hosomi, A. Tetrahedron Lett. 1993, 34, 8123. Knölker, H.-J.; Baum, G.; Graf, R. Angew. Chem., Int. Ed. Engl. 1994, 33, 1612. Monti, H.; Audran, G.; Léandri, G.; Monti, J.-P. Tetrahedron Lett. 1994, 35, 3073. Monti, H.; Audran, G.; Monti, J.-P.; Léandri, G. Synlett 1994, 403. Brengel, G. P.; Rithner, C.; Meyers, A. I. J. Org. Chem. 1994, 59, 5144.
22. Recently, construction of cyclobutanes by Lewis acid promoted [2+2] cycloaddition of allylsilanes to α,β-unsaturated carbonyl compounds have been reported; Hojo, M.; Tomita, K.; Hirohara, Y.; Hosomi, A. Tetrahedron Lett. 1993, 34, 8123. Knölker, H.-J.; Baum, G.; Graf, R. Angew. Chem., Int. Ed. Engl. 1994, 33, 1612. Monti, H.; Audran, G.; Léandri, G.; Monti, J.-P. Tetrahedron Lett. 1994, 35, 3073. Monti, H.; Audran, G.; Monti, J.-P.; Léandri, G. Synlett 1994, 403. Brengel, G. P.; Rithner, C.; Meyers, A. I. J. Org. Chem. 1994, 59, 5144.
23. Recently, construction of cyclobutanes by Lewis acid promoted [2+2] cycloaddition of allylsilanes to α,β-unsaturated carbonyl compounds have been reported; Hojo, M.; Tomita, K.; Hirohara, Y.; Hosomi, A. Tetrahedron Lett. 1993, 34, 8123. Knölker, H.-J.; Baum, G.; Graf, R. Angew. Chem., Int. Ed. Engl. 1994, 33, 1612. Monti, H.; Audran, G.; Léandri, G.; Monti, J.-P. Tetrahedron Lett. 1994, 35, 3073. Monti, H.; Audran, G.; Monti, J.-P.; Léandri, G. Synlett 1994, 403. Brengel, G. P.; Rithner, C.; Meyers, A. I. J. Org. Chem. 1994, 59, 5144.
24. Recently, construction of cyclobutanes by Lewis acid promoted [2+2] cycloaddition of allylsilanes to α,β-unsaturated carbonyl compounds have been reported; Hojo, M.; Tomita, K.; Hirohara, Y.; Hosomi, A. Tetrahedron Lett. 1993, 34, 8123. Knölker, H.-J.; Baum, G.; Graf, R. Angew. Chem., Int. Ed. Engl. 1994, 33, 1612. Monti, H.; Audran, G.; Léandri, G.; Monti, J.-P. Tetrahedron Lett. 1994, 35, 3073. Monti, H.; Audran, G.; Monti, J.-P.; Léandri, G. Synlett 1994, 403. Brengel, G. P.; Rithner, C.; Meyers, A. I. J. Org. Chem. 1994, 59, 5144.
25. Recently, construction of cyclobutanes by Lewis acid promoted [2+2] cycloaddition of allylsilanes to α,β-unsaturated carbonyl compounds have been reported; Hojo, M.; Tomita, K.; Hirohara, Y.; Hosomi, A. Tetrahedron Lett. 1993, 34, 8123. Knölker, H.-J.; Baum, G.; Graf, R. Angew. Chem., Int. Ed. Engl. 1994, 33, 1612. Monti, H.; Audran, G.; Léandri, G.; Monti, J.-P. Tetrahedron Lett. 1994, 35, 3073. Monti, H.; Audran, G.; Monti, J.-P.; Léandri, G. Synlett 1994, 403. Brengel, G. P.; Rithner, C.; Meyers, A. I. J. Org. Chem. 1994, 59, 5144.
26. Heathcock, C. H.; Kiyooka, S.; Blumenkopf, T. A. J. Org. Chem. 1984, 49, 4214.