Intramolecular Diels-Alder Reaction of Furans with Allenyl Ethers Followed by Sulfur and Silicon Atom-Containing Group Rearrangement

Journal of Organic Chemistry

Volumn 63, Issue 15, 1998, Pages 5064-5070

  Wu, Hsien Jen ^a   Yen, Chia Hui ^a   Chuang, Chi Te ^a  

^a NATIONAL CHIAO TUNG UNIVERSITY   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000793177     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo980240l     Document Type: Article

References (30)

1. For reviews, see: (a) Oppolzer, W. Angew. Chem., Int. Ed. Engl. 1977, 16, 10. (b) Brieger, G.; Bennett, J. N. Chem. Rev. 1980, 80, 63. (c) Fallis, A. G. Can. J. Chem. 1984, 62, 183. (d) Ciganek, E. Org. React. 1984, 32, 1. (e) Weinreb, S. M.; Staib, R. R. Tetrahedron 1982, 38, 3087. (f) Weinreb, S. M. Acc. Chem. Res. 1985, 78, 16. (g) Craig, D. Chem. Soc. Rev. 1987, 16, 187.
2. For reviews, see: (a) Oppolzer, W. Angew. Chem., Int. Ed. Engl. 1977, 16, 10. (b) Brieger, G.; Bennett, J. N. Chem. Rev. 1980, 80, 63. (c) Fallis, A. G. Can. J. Chem. 1984, 62, 183. (d) Ciganek, E. Org. React. 1984, 32, 1. (e) Weinreb, S. M.; Staib, R. R. Tetrahedron 1982, 38, 3087. (f) Weinreb, S. M. Acc. Chem. Res. 1985, 78, 16. (g) Craig, D. Chem. Soc. Rev. 1987, 16, 187.
3. For reviews, see: (a) Oppolzer, W. Angew. Chem., Int. Ed. Engl. 1977, 16, 10. (b) Brieger, G.; Bennett, J. N. Chem. Rev. 1980, 80, 63. (c) Fallis, A. G. Can. J. Chem. 1984, 62, 183. (d) Ciganek, E. Org. React. 1984, 32, 1. (e) Weinreb, S. M.; Staib, R. R. Tetrahedron 1982, 38, 3087. (f) Weinreb, S. M. Acc. Chem. Res. 1985, 78, 16. (g) Craig, D. Chem. Soc. Rev. 1987, 16, 187.
4. For reviews, see: (a) Oppolzer, W. Angew. Chem., Int. Ed. Engl. 1977, 16, 10. (b) Brieger, G.; Bennett, J. N. Chem. Rev. 1980, 80, 63. (c) Fallis, A. G. Can. J. Chem. 1984, 62, 183. (d) Ciganek, E. Org. React. 1984, 32, 1. (e) Weinreb, S. M.; Staib, R. R. Tetrahedron 1982, 38, 3087. (f) Weinreb, S. M. Acc. Chem. Res. 1985, 78, 16. (g) Craig, D. Chem. Soc. Rev. 1987, 16, 187.
5. For reviews, see: (a) Oppolzer, W. Angew. Chem., Int. Ed. Engl. 1977, 16, 10. (b) Brieger, G.; Bennett, J. N. Chem. Rev. 1980, 80, 63. (c) Fallis, A. G. Can. J. Chem. 1984, 62, 183. (d) Ciganek, E. Org. React. 1984, 32, 1. (e) Weinreb, S. M.; Staib, R. R. Tetrahedron 1982, 38, 3087. (f) Weinreb, S. M. Acc. Chem. Res. 1985, 78, 16. (g) Craig, D. Chem. Soc. Rev. 1987, 16, 187.
6. For reviews, see: (a) Oppolzer, W. Angew. Chem., Int. Ed. Engl. 1977, 16, 10. (b) Brieger, G.; Bennett, J. N. Chem. Rev. 1980, 80, 63. (c) Fallis, A. G. Can. J. Chem. 1984, 62, 183. (d) Ciganek, E. Org. React. 1984, 32, 1. (e) Weinreb, S. M.; Staib, R. R. Tetrahedron 1982, 38, 3087. (f) Weinreb, S. M. Acc. Chem. Res. 1985, 78, 16. (g) Craig, D. Chem. Soc. Rev. 1987, 16, 187.
7. For reviews, see: (a) Oppolzer, W. Angew. Chem., Int. Ed. Engl. 1977, 16, 10. (b) Brieger, G.; Bennett, J. N. Chem. Rev. 1980, 80, 63. (c) Fallis, A. G. Can. J. Chem. 1984, 62, 183. (d) Ciganek, E. Org. React. 1984, 32, 1. (e) Weinreb, S. M.; Staib, R. R. Tetrahedron 1982, 38, 3087. (f) Weinreb, S. M. Acc. Chem. Res. 1985, 78, 16. (g) Craig, D. Chem. Soc. Rev. 1987, 16, 187.
8. For some examples of the intramolecular Diels-Alder reactions of allenic dienophiles, see: (a) Bartlett, A. J.; Laird, T.; Ollis, W. D. J. Chem. Soc., Perkin Trans. 1 1975, 1315. (b) Himbert, G.; Diehl, K.; Maas, G. J. Chem. Soc., Chem. Commun. 1984, 900. (c) Harrison, R. M.; Hobson, J. D.; Midgley, A. W. J. Chem. Soc., Perkin Trans. 1 1973, 1960. (d) Saxton, H. M.; Sutherland, J. K.; Whaley, C. J. Chem. Soc., Chem. Commun. 1987, 1449. (e) Hayakawa, K.; Yasukouchi, T.; Kanematus, K. Tetrahedron Lett. 1986, 27, 1837. (f) Hayakawa, K.; Nagatsugi, F.; Kanematsu, K. J. Org. Chem. 1988, 53, 860. (g) Hayakawa, K.; Yasukouchi, T.; Kanematsu, K. Tertahedron Lett. 1987, 28, 5895. (h) Yasukouchi, T.; Kanematsu, K. Tetrahedron Lett. 1989, 30, 6559. (i) Yoshida, M.; Hiromatsu, M.; Kanematsu, K. Heterocycles 1986, 24, 881. (j) Hayakawa, K.; Ohsuki, S.; Kanematsu, K. Tetrahedron Lett. 1986, 27, 947.
9. For some examples of the intramolecular Diels-Alder reactions of allenic dienophiles, see: (a) Bartlett, A. J.; Laird, T.; Ollis, W. D. J. Chem. Soc., Perkin Trans. 1 1975, 1315. (b) Himbert, G.; Diehl, K.; Maas, G. J. Chem. Soc., Chem. Commun. 1984, 900. (c) Harrison, R. M.; Hobson, J. D.; Midgley, A. W. J. Chem. Soc., Perkin Trans. 1 1973, 1960. (d) Saxton, H. M.; Sutherland, J. K.; Whaley, C. J. Chem. Soc., Chem. Commun. 1987, 1449. (e) Hayakawa, K.; Yasukouchi, T.; Kanematus, K. Tetrahedron Lett. 1986, 27, 1837. (f) Hayakawa, K.; Nagatsugi, F.; Kanematsu, K. J. Org. Chem. 1988, 53, 860. (g) Hayakawa, K.; Yasukouchi, T.; Kanematsu, K. Tertahedron Lett. 1987, 28, 5895. (h) Yasukouchi, T.; Kanematsu, K. Tetrahedron Lett. 1989, 30, 6559. (i) Yoshida, M.; Hiromatsu, M.; Kanematsu, K. Heterocycles 1986, 24, 881. (j) Hayakawa, K.; Ohsuki, S.; Kanematsu, K. Tetrahedron Lett. 1986, 27, 947.
10. For some examples of the intramolecular Diels-Alder reactions of allenic dienophiles, see: (a) Bartlett, A. J.; Laird, T.; Ollis, W. D. J. Chem. Soc., Perkin Trans. 1 1975, 1315. (b) Himbert, G.; Diehl, K.; Maas, G. J. Chem. Soc., Chem. Commun. 1984, 900. (c) Harrison, R. M.; Hobson, J. D.; Midgley, A. W. J. Chem. Soc., Perkin Trans. 1 1973, 1960. (d) Saxton, H. M.; Sutherland, J. K.; Whaley, C. J. Chem. Soc., Chem. Commun. 1987, 1449. (e) Hayakawa, K.; Yasukouchi, T.; Kanematus, K. Tetrahedron Lett. 1986, 27, 1837. (f) Hayakawa, K.; Nagatsugi, F.; Kanematsu, K. J. Org. Chem. 1988, 53, 860. (g) Hayakawa, K.; Yasukouchi, T.; Kanematsu, K. Tertahedron Lett. 1987, 28, 5895. (h) Yasukouchi, T.; Kanematsu, K. Tetrahedron Lett. 1989, 30, 6559. (i) Yoshida, M.; Hiromatsu, M.; Kanematsu, K. Heterocycles 1986, 24, 881. (j) Hayakawa, K.; Ohsuki, S.; Kanematsu, K. Tetrahedron Lett. 1986, 27, 947.
11. For some examples of the intramolecular Diels-Alder reactions of allenic dienophiles, see: (a) Bartlett, A. J.; Laird, T.; Ollis, W. D. J. Chem. Soc., Perkin Trans. 1 1975, 1315. (b) Himbert, G.; Diehl, K.; Maas, G. J. Chem. Soc., Chem. Commun. 1984, 900. (c) Harrison, R. M.; Hobson, J. D.; Midgley, A. W. J. Chem. Soc., Perkin Trans. 1 1973, 1960. (d) Saxton, H. M.; Sutherland, J. K.; Whaley, C. J. Chem. Soc., Chem. Commun. 1987, 1449. (e) Hayakawa, K.; Yasukouchi, T.; Kanematus, K. Tetrahedron Lett. 1986, 27, 1837. (f) Hayakawa, K.; Nagatsugi, F.; Kanematsu, K. J. Org. Chem. 1988, 53, 860. (g) Hayakawa, K.; Yasukouchi, T.; Kanematsu, K. Tertahedron Lett. 1987, 28, 5895. (h) Yasukouchi, T.; Kanematsu, K. Tetrahedron Lett. 1989, 30, 6559. (i) Yoshida, M.; Hiromatsu, M.; Kanematsu, K. Heterocycles 1986, 24, 881. (j) Hayakawa, K.; Ohsuki, S.; Kanematsu, K. Tetrahedron Lett. 1986, 27, 947.
12. For some examples of the intramolecular Diels-Alder reactions of allenic dienophiles, see: (a) Bartlett, A. J.; Laird, T.; Ollis, W. D. J. Chem. Soc., Perkin Trans. 1 1975, 1315. (b) Himbert, G.; Diehl, K.; Maas, G. J. Chem. Soc., Chem. Commun. 1984, 900. (c) Harrison, R. M.; Hobson, J. D.; Midgley, A. W. J. Chem. Soc., Perkin Trans. 1 1973, 1960. (d) Saxton, H. M.; Sutherland, J. K.; Whaley, C. J. Chem. Soc., Chem. Commun. 1987, 1449. (e) Hayakawa, K.; Yasukouchi, T.; Kanematus, K. Tetrahedron Lett. 1986, 27, 1837. (f) Hayakawa, K.; Nagatsugi, F.; Kanematsu, K. J. Org. Chem. 1988, 53, 860. (g) Hayakawa, K.; Yasukouchi, T.; Kanematsu, K. Tertahedron Lett. 1987, 28, 5895. (h) Yasukouchi, T.; Kanematsu, K. Tetrahedron Lett. 1989, 30, 6559. (i) Yoshida, M.; Hiromatsu, M.; Kanematsu, K. Heterocycles 1986, 24, 881. (j) Hayakawa, K.; Ohsuki, S.; Kanematsu, K. Tetrahedron Lett. 1986, 27, 947.
13. For some examples of the intramolecular Diels-Alder reactions of allenic dienophiles, see: (a) Bartlett, A. J.; Laird, T.; Ollis, W. D. J. Chem. Soc., Perkin Trans. 1 1975, 1315. (b) Himbert, G.; Diehl, K.; Maas, G. J. Chem. Soc., Chem. Commun. 1984, 900. (c) Harrison, R. M.; Hobson, J. D.; Midgley, A. W. J. Chem. Soc., Perkin Trans. 1 1973, 1960. (d) Saxton, H. M.; Sutherland, J. K.; Whaley, C. J. Chem. Soc., Chem. Commun. 1987, 1449. (e) Hayakawa, K.; Yasukouchi, T.; Kanematus, K. Tetrahedron Lett. 1986, 27, 1837. (f) Hayakawa, K.; Nagatsugi, F.; Kanematsu, K. J. Org. Chem. 1988, 53, 860. (g) Hayakawa, K.; Yasukouchi, T.; Kanematsu, K. Tertahedron Lett. 1987, 28, 5895. (h) Yasukouchi, T.; Kanematsu, K. Tetrahedron Lett. 1989, 30, 6559. (i) Yoshida, M.; Hiromatsu, M.; Kanematsu, K. Heterocycles 1986, 24, 881. (j) Hayakawa, K.; Ohsuki, S.; Kanematsu, K. Tetrahedron Lett. 1986, 27, 947.
14. For some examples of the intramolecular Diels-Alder reactions of allenic dienophiles, see: (a) Bartlett, A. J.; Laird, T.; Ollis, W. D. J. Chem. Soc., Perkin Trans. 1 1975, 1315. (b) Himbert, G.; Diehl, K.; Maas, G. J. Chem. Soc., Chem. Commun. 1984, 900. (c) Harrison, R. M.; Hobson, J. D.; Midgley, A. W. J. Chem. Soc., Perkin Trans. 1 1973, 1960. (d) Saxton, H. M.; Sutherland, J. K.; Whaley, C. J. Chem. Soc., Chem. Commun. 1987, 1449. (e) Hayakawa, K.; Yasukouchi, T.; Kanematus, K. Tetrahedron Lett. 1986, 27, 1837. (f) Hayakawa, K.; Nagatsugi, F.; Kanematsu, K. J. Org. Chem. 1988, 53, 860. (g) Hayakawa, K.; Yasukouchi, T.; Kanematsu, K. Tertahedron Lett. 1987, 28, 5895. (h) Yasukouchi, T.; Kanematsu, K. Tetrahedron Lett. 1989, 30, 6559. (i) Yoshida, M.; Hiromatsu, M.; Kanematsu, K. Heterocycles 1986, 24, 881. (j) Hayakawa, K.; Ohsuki, S.; Kanematsu, K. Tetrahedron Lett. 1986, 27, 947.
15. For some examples of the intramolecular Diels-Alder reactions of allenic dienophiles, see: (a) Bartlett, A. J.; Laird, T.; Ollis, W. D. J. Chem. Soc., Perkin Trans. 1 1975, 1315. (b) Himbert, G.; Diehl, K.; Maas, G. J. Chem. Soc., Chem. Commun. 1984, 900. (c) Harrison, R. M.; Hobson, J. D.; Midgley, A. W. J. Chem. Soc., Perkin Trans. 1 1973, 1960. (d) Saxton, H. M.; Sutherland, J. K.; Whaley, C. J. Chem. Soc., Chem. Commun. 1987, 1449. (e) Hayakawa, K.; Yasukouchi, T.; Kanematus, K. Tetrahedron Lett. 1986, 27, 1837. (f) Hayakawa, K.; Nagatsugi, F.; Kanematsu, K. J. Org. Chem. 1988, 53, 860. (g) Hayakawa, K.; Yasukouchi, T.; Kanematsu, K. Tertahedron Lett. 1987, 28, 5895. (h) Yasukouchi, T.; Kanematsu, K. Tetrahedron Lett. 1989, 30, 6559. (i) Yoshida, M.; Hiromatsu, M.; Kanematsu, K. Heterocycles 1986, 24, 881. (j) Hayakawa, K.; Ohsuki, S.; Kanematsu, K. Tetrahedron Lett. 1986, 27, 947.
16. For some examples of the intramolecular Diels-Alder reactions of allenic dienophiles, see: (a) Bartlett, A. J.; Laird, T.; Ollis, W. D. J. Chem. Soc., Perkin Trans. 1 1975, 1315. (b) Himbert, G.; Diehl, K.; Maas, G. J. Chem. Soc., Chem. Commun. 1984, 900. (c) Harrison, R. M.; Hobson, J. D.; Midgley, A. W. J. Chem. Soc., Perkin Trans. 1 1973, 1960. (d) Saxton, H. M.; Sutherland, J. K.; Whaley, C. J. Chem. Soc., Chem. Commun. 1987, 1449. (e) Hayakawa, K.; Yasukouchi, T.; Kanematus, K. Tetrahedron Lett. 1986, 27, 1837. (f) Hayakawa, K.; Nagatsugi, F.; Kanematsu, K. J. Org. Chem. 1988, 53, 860. (g) Hayakawa, K.; Yasukouchi, T.; Kanematsu, K. Tertahedron Lett. 1987, 28, 5895. (h) Yasukouchi, T.; Kanematsu, K. Tetrahedron Lett. 1989, 30, 6559. (i) Yoshida, M.; Hiromatsu, M.; Kanematsu, K. Heterocycles 1986, 24, 881. (j) Hayakawa, K.; Ohsuki, S.; Kanematsu, K. Tetrahedron Lett. 1986, 27, 947.
17. For some examples of the intramolecular Diels-Alder reactions of allenic dienophiles, see: (a) Bartlett, A. J.; Laird, T.; Ollis, W. D. J. Chem. Soc., Perkin Trans. 1 1975, 1315. (b) Himbert, G.; Diehl, K.; Maas, G. J. Chem. Soc., Chem. Commun. 1984, 900. (c) Harrison, R. M.; Hobson, J. D.; Midgley, A. W. J. Chem. Soc., Perkin Trans. 1 1973, 1960. (d) Saxton, H. M.; Sutherland, J. K.; Whaley, C. J. Chem. Soc., Chem. Commun. 1987, 1449. (e) Hayakawa, K.; Yasukouchi, T.; Kanematus, K. Tetrahedron Lett. 1986, 27, 1837. (f) Hayakawa, K.; Nagatsugi, F.; Kanematsu, K. J. Org. Chem. 1988, 53, 860. (g) Hayakawa, K.; Yasukouchi, T.; Kanematsu, K. Tertahedron Lett. 1987, 28, 5895. (h) Yasukouchi, T.; Kanematsu, K. Tetrahedron Lett. 1989, 30, 6559. (i) Yoshida, M.; Hiromatsu, M.; Kanematsu, K. Heterocycles 1986, 24, 881. (j) Hayakawa, K.; Ohsuki, S.; Kanematsu, K. Tetrahedron Lett. 1986, 27, 947.
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29. The author has deposited atomic coordinates for 10a with the Cambridge Crystallographic Data Center. The coordinates can be obtained, on request, from the Director, Cambridge Crystallogriphic Data Center, 12 Union Road, Cambridge, CB2 1EZ, UK.
30. Brook, A. G. Acc. Chem. Res. 1974, 7, 77.