Asymmetric synthesis by vapor phase pyrolysis

Tetrahedron Letters

Volumn 44, Issue 15, 2003, Pages 3115-3117

  Sugimura, Takashi ^a   Tei, Takahiro ^a   Okuyama, Tadashi ^a  

^a UNIVERSITY OF HYOGO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

2,4 PENTANEDIOL; CYCLOHEXENE DERIVATIVE; ESTER DERIVATIVE; KETENE DERIVATIVE; PENTANE; UNCLASSIFIED DRUG;

ARTICLE; ASYMMETRIC SYNTHESIS; CYCLOADDITION; ENTROPY; HIGH TEMPERATURE; PYROLYSIS; STEREOCHEMISTRY; VAPOR;

EID: 0037424791     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)00549-5     Document Type: Article

References (29)

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2. For recent examples, see: (a) Sugimura, T.; Nagano, S.; Tai, A. Chem. Lett. 1998, 45-46; (b) Yamaguchi, K.; Sugimura, T.; Nishida, F.; Tai, A. Tetrahedron Lett. 1998, 39, 4521-4524; (c) Fujita, M.; Matsushima, H.; Sugimura, T.; Tai, A.; Okuyama, T. J. Am. Chem. Soc. 2001, 123, 2946-2956.
3. For recent examples, see: (a) Sugimura, T.; Nagano, S.; Tai, A. Chem. Lett. 1998, 45-46; (b) Yamaguchi, K.; Sugimura, T.; Nishida, F.; Tai, A. Tetrahedron Lett. 1998, 39, 4521-4524; (c) Fujita, M.; Matsushima, H.; Sugimura, T.; Tai, A.; Okuyama, T. J. Am. Chem. Soc. 2001, 123, 2946-2956.
4. For recent examples, see: (a) Sugimura, T.; Nagano, S.; Tai, A. Chem. Lett. 1998, 45-46; (b) Yamaguchi, K.; Sugimura, T.; Nishida, F.; Tai, A. Tetrahedron Lett. 1998, 39, 4521-4524; (c) Fujita, M.; Matsushima, H.; Sugimura, T.; Tai, A.; Okuyama, T. J. Am. Chem. Soc. 2001, 123, 2946-2956.
5. Sugimura T., Tei T., Mori A., Okuyama T., Tai A. J. Am. Chem. Soc. 122:2000;2128-2129.
6. Importance of the entropy term in asymmetric synthesis has also been pointed out for other reactions. See: (a) Buschmann, H.; Scharf, H. D.; Hoffmann, N.; Esser, P. Angew. Chem., Int. Ed. Engl. 1991, 30, 477-515; (b) Otera, J.; Sakamoto, K.; Tsukamoto, T.; Orita, A. Tetrahedron Lett. 1998, 39, 3201-3204; (c) Inoue, Y.; Ikeda, H.; Kaneda, M.; Sumimura, T.; Everitt, S. R. L.; Wada, T. J. Am. Chem. Soc. 2000, 122, 406-40; Inoue, Y.; Sugahara, N.; Wada, T. Pure Appl. Chem. 2001, 73, 475-40; (d) Nishida, T.; Miyafuji, A.; Ito, Y. N.; Katsuki, T. Tetrahedron Lett. 2000, 41, 7053-7058; (e) Sugimura, T.; Hagiya, K.; Sato, Y.; Tei, T.; Tai, A.; Okuyama, T. Org. Lett. 2001, 3, 37-40; Tei, T.; Sato, Y.; Hagiya, K.; Tai, A.; Okuyama, T.; Sugimura, T. J. Org. Chem. 2002, 67, 6593-6598.
7. Importance of the entropy term in asymmetric synthesis has also been pointed out for other reactions. See: (a) Buschmann, H.; Scharf, H. D.; Hoffmann, N.; Esser, P. Angew. Chem., Int. Ed. Engl. 1991, 30, 477-515; (b) Otera, J.; Sakamoto, K.; Tsukamoto, T.; Orita, A. Tetrahedron Lett. 1998, 39, 3201-3204; (c) Inoue, Y.; Ikeda, H.; Kaneda, M.; Sumimura, T.; Everitt, S. R. L.; Wada, T. J. Am. Chem. Soc. 2000, 122, 406-40; Inoue, Y.; Sugahara, N.; Wada, T. Pure Appl. Chem. 2001, 73, 475-40; (d) Nishida, T.; Miyafuji, A.; Ito, Y. N.; Katsuki, T. Tetrahedron Lett. 2000, 41, 7053-7058; (e) Sugimura, T.; Hagiya, K.; Sato, Y.; Tei, T.; Tai, A.; Okuyama, T. Org. Lett. 2001, 3, 37-40; Tei, T.; Sato, Y.; Hagiya, K.; Tai, A.; Okuyama, T.; Sugimura, T. J. Org. Chem. 2002, 67, 6593-6598.
8. Importance of the entropy term in asymmetric synthesis has also been pointed out for other reactions. See: (a) Buschmann, H.; Scharf, H. D.; Hoffmann, N.; Esser, P. Angew. Chem., Int. Ed. Engl. 1991, 30, 477-515; (b) Otera, J.; Sakamoto, K.; Tsukamoto, T.; Orita, A. Tetrahedron Lett. 1998, 39, 3201-3204; (c) Inoue, Y.; Ikeda, H.; Kaneda, M.; Sumimura, T.; Everitt, S. R. L.; Wada, T. J. Am. Chem. Soc. 2000, 122, 406-40; Inoue, Y.; Sugahara, N.; Wada, T. Pure Appl. Chem. 2001, 73, 475-40; (d) Nishida, T.; Miyafuji, A.; Ito, Y. N.; Katsuki, T. Tetrahedron Lett. 2000, 41, 7053-7058; (e) Sugimura, T.; Hagiya, K.; Sato, Y.; Tei, T.; Tai, A.; Okuyama, T. Org. Lett. 2001, 3, 37-40; Tei, T.; Sato, Y.; Hagiya, K.; Tai, A.; Okuyama, T.; Sugimura, T. J. Org. Chem. 2002, 67, 6593-6598.
9. Importance of the entropy term in asymmetric synthesis has also been pointed out for other reactions. See: (a) Buschmann, H.; Scharf, H. D.; Hoffmann, N.; Esser, P. Angew. Chem., Int. Ed. Engl. 1991, 30, 477-515; (b) Otera, J.; Sakamoto, K.; Tsukamoto, T.; Orita, A. Tetrahedron Lett. 1998, 39, 3201-3204; (c) Inoue, Y.; Ikeda, H.; Kaneda, M.; Sumimura, T.; Everitt, S. R. L.; Wada, T. J. Am. Chem. Soc. 2000, 122, 406-40; Inoue, Y.; Sugahara, N.; Wada, T. Pure Appl. Chem. 2001, 73, 475-40; (d) Nishida, T.; Miyafuji, A.; Ito, Y. N.; Katsuki, T. Tetrahedron Lett. 2000, 41, 7053-7058; (e) Sugimura, T.; Hagiya, K.; Sato, Y.; Tei, T.; Tai, A.; Okuyama, T. Org. Lett. 2001, 3, 37-40; Tei, T.; Sato, Y.; Hagiya, K.; Tai, A.; Okuyama, T.; Sugimura, T. J. Org. Chem. 2002, 67, 6593-6598.
10. Importance of the entropy term in asymmetric synthesis has also been pointed out for other reactions. See: (a) Buschmann, H.; Scharf, H. D.; Hoffmann, N.; Esser, P. Angew. Chem., Int. Ed. Engl. 1991, 30, 477-515; (b) Otera, J.; Sakamoto, K.; Tsukamoto, T.; Orita, A. Tetrahedron Lett. 1998, 39, 3201-3204; (c) Inoue, Y.; Ikeda, H.; Kaneda, M.; Sumimura, T.; Everitt, S. R. L.; Wada, T. J. Am. Chem. Soc. 2000, 122, 406-40; Inoue, Y.; Sugahara, N.; Wada, T. Pure Appl. Chem. 2001, 73, 475-40; (d) Nishida, T.; Miyafuji, A.; Ito, Y. N.; Katsuki, T. Tetrahedron Lett. 2000, 41, 7053-7058; (e) Sugimura, T.; Hagiya, K.; Sato, Y.; Tei, T.; Tai, A.; Okuyama, T. Org. Lett. 2001, 3, 37-40; Tei, T.; Sato, Y.; Hagiya, K.; Tai, A.; Okuyama, T.; Sugimura, T. J. Org. Chem. 2002, 67, 6593-6598.
11. Importance of the entropy term in asymmetric synthesis has also been pointed out for other reactions. See: (a) Buschmann, H.; Scharf, H. D.; Hoffmann, N.; Esser, P. Angew. Chem., Int. Ed. Engl. 1991, 30, 477-515; (b) Otera, J.; Sakamoto, K.; Tsukamoto, T.; Orita, A. Tetrahedron Lett. 1998, 39, 3201-3204; (c) Inoue, Y.; Ikeda, H.; Kaneda, M.; Sumimura, T.; Everitt, S. R. L.; Wada, T. J. Am. Chem. Soc. 2000, 122, 406-40; Inoue, Y.; Sugahara, N.; Wada, T. Pure Appl. Chem. 2001, 73, 475-40; (d) Nishida, T.; Miyafuji, A.; Ito, Y. N.; Katsuki, T. Tetrahedron Lett. 2000, 41, 7053-7058; (e) Sugimura, T.; Hagiya, K.; Sato, Y.; Tei, T.; Tai, A.; Okuyama, T. Org. Lett. 2001, 3, 37-40; Tei, T.; Sato, Y.; Hagiya, K.; Tai, A.; Okuyama, T.; Sugimura, T. J. Org. Chem. 2002, 67, 6593-6598.
12. Importance of the entropy term in asymmetric synthesis has also been pointed out for other reactions. See: (a) Buschmann, H.; Scharf, H. D.; Hoffmann, N.; Esser, P. Angew. Chem., Int. Ed. Engl. 1991, 30, 477-515; (b) Otera, J.; Sakamoto, K.; Tsukamoto, T.; Orita, A. Tetrahedron Lett. 1998, 39, 3201-3204; (c) Inoue, Y.; Ikeda, H.; Kaneda, M.; Sumimura, T.; Everitt, S. R. L.; Wada, T. J. Am. Chem. Soc. 2000, 122, 406-40; Inoue, Y.; Sugahara, N.; Wada, T. Pure Appl. Chem. 2001, 73, 475-40; (d) Nishida, T.; Miyafuji, A.; Ito, Y. N.; Katsuki, T. Tetrahedron Lett. 2000, 41, 7053-7058; (e) Sugimura, T.; Hagiya, K.; Sato, Y.; Tei, T.; Tai, A.; Okuyama, T. Org. Lett. 2001, 3, 37-40; Tei, T.; Sato, Y.; Hagiya, K.; Tai, A.; Okuyama, T.; Sugimura, T. J. Org. Chem. 2002, 67, 6593-6598.
13. For general references, see: (a) Eliel, E. L. Stereoselectivity of Carbon Compounds; MacGraw-Hill: New York, 1962; pp. 151-152, 237-239; (b) Seyden-Penne, J. Chiral Auxiliaries and Ligands in Asymmetric Synthesis; Wiley: New York, 1995; pp. 1-6; (c) Nogradi, M. Stereoselective Synthesis; VCH: Weinheim, 1995; pp. 41-43; (d) Gawley, R. E. Principles of Asymmetric Synthesis; Pergamon: Oxford, 1996; pp. 7-10.
14. For general references, see: (a) Eliel, E. L. Stereoselectivity of Carbon Compounds; MacGraw-Hill: New York, 1962; pp. 151-152, 237-239; (b) Seyden-Penne, J. Chiral Auxiliaries and Ligands in Asymmetric Synthesis; Wiley: New York, 1995; pp. 1-6; (c) Nogradi, M. Stereoselective Synthesis; VCH: Weinheim, 1995; pp. 41-43; (d) Gawley, R. E. Principles of Asymmetric Synthesis; Pergamon: Oxford, 1996; pp. 7-10.
15. For general references, see: (a) Eliel, E. L. Stereoselectivity of Carbon Compounds; MacGraw-Hill: New York, 1962; pp. 151-152, 237-239; (b) Seyden-Penne, J. Chiral Auxiliaries and Ligands in Asymmetric Synthesis; Wiley: New York, 1995; pp. 1-6; (c) Nogradi, M. Stereoselective Synthesis; VCH: Weinheim, 1995; pp. 41-43; (d) Gawley, R. E. Principles of Asymmetric Synthesis; Pergamon: Oxford, 1996; pp. 7-10.
16. For general references, see: (a) Eliel, E. L. Stereoselectivity of Carbon Compounds; MacGraw-Hill: New York, 1962; pp. 151-152, 237-239; (b) Seyden-Penne, J. Chiral Auxiliaries and Ligands in Asymmetric Synthesis; Wiley: New York, 1995; pp. 1-6; (c) Nogradi, M. Stereoselective Synthesis; VCH: Weinheim, 1995; pp. 41-43; (d) Gawley, R. E. Principles of Asymmetric Synthesis; Pergamon: Oxford, 1996; pp. 7-10.
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23. The cycloaddition was confirmed to occur in the vapor phase. When methanol was placed at the cold trap prior to the pyrolysis of 1, only 2 (and 3) was obtained, but no methanol adduct was obtained. The reaction of the ketene intermediate with methanol was proved to be faster than the intramolecular cycloaddition by the photolysis of 1 in a solvent containing methanol.
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27. For recent studies, see: (c) Toscano, J. P.; Platz, M. S. J. Am. Chem. Soc. 1995, 117, 4712-4713; (d) Chiang, Y.; Kresge, A. J.; Popik, V. V. J. Am. Chem. Soc. 1999, 121, 5930-5032; (e) Wang, Y.; Toscano, J. P. J. Am. Chem. Soc. 2000, 122, 4512-4513.
28. For recent studies, see: (c) Toscano, J. P.; Platz, M. S. J. Am. Chem. Soc. 1995, 117, 4712-4713; (d) Chiang, Y.; Kresge, A. J.; Popik, V. V. J. Am. Chem. Soc. 1999, 121, 5930-5032; (e) Wang, Y.; Toscano, J. P. J. Am. Chem. Soc. 2000, 122, 4512-4513.
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