Tandem annulations: A one operation construction of bicyclo[3.3.0]octan-1-ol and bicyclo[3.2.1]octan-1-ol skeletons by a three-component coupling reaction of alk-4-enyl iodides with CO and alkenes in the presence of zinc

Chemical Communications

Volumn , Issue 19, 1997, Pages 1889-1890

  Tsunoi, Shinji ^a   Ryu, Ilhyong ^a   Yamasaki, Sumiaki ^a   Tanaka, Minoru ^a   Sonoda, Noboru ^a,b   Komatsu, Mitsuo ^a  

^a OSAKA UNIVERSITY   (Japan)

^b KANSAI UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002713758     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/a704934j     Document Type: Article

References (24)

1. I. Ryu, N. Sonoda and D. P. Curran, Chem. Rev., 1996, 96, 177; I. Ryu and N. Sonoda, Angew. Chem., Int. Ed. Engl., 1996, 35, 1050.
2. I. Ryu, N. Sonoda and D. P. Curran, Chem. Rev., 1996, 96, 177; I. Ryu and N. Sonoda, Angew. Chem., Int. Ed. Engl., 1996, 35, 1050.
3. S. Tsunoi, I. Ryu, H. Fukushima, M. Tanaka, M. Komatsu and N. Sonoda, Synlett, 1995, 1249.
4. For reviews, see G. A. Molander, Chem. Rev., 1992, 92, 29; D. P. Curran, T. L. Fevig, C. P. Jasperse and M. J. Totleben, Synlett, 1992, 943; J. Iqbal, B. Bhatia and N. K. Nayyar, Chem. Rev., 1994, 59, 519; P. I. Dalko, Tetrahedron, 1995, 51, 7579; G. A. Molander and C. R. Harris, Chem. Rev., 1996, 96, 307.
5. For reviews, see G. A. Molander, Chem. Rev., 1992, 92, 29; D. P. Curran, T. L. Fevig, C. P. Jasperse and M. J. Totleben, Synlett, 1992, 943; J. Iqbal, B. Bhatia and N. K. Nayyar, Chem. Rev., 1994, 59, 519; P. I. Dalko, Tetrahedron, 1995, 51, 7579; G. A. Molander and C. R. Harris, Chem. Rev., 1996, 96, 307.
6. For reviews, see G. A. Molander, Chem. Rev., 1992, 92, 29; D. P. Curran, T. L. Fevig, C. P. Jasperse and M. J. Totleben, Synlett, 1992, 943; J. Iqbal, B. Bhatia and N. K. Nayyar, Chem. Rev., 1994, 59, 519; P. I. Dalko, Tetrahedron, 1995, 51, 7579; G. A. Molander and C. R. Harris, Chem. Rev., 1996, 96, 307.
7. For reviews, see G. A. Molander, Chem. Rev., 1992, 92, 29; D. P. Curran, T. L. Fevig, C. P. Jasperse and M. J. Totleben, Synlett, 1992, 943; J. Iqbal, B. Bhatia and N. K. Nayyar, Chem. Rev., 1994, 59, 519; P. I. Dalko, Tetrahedron, 1995, 51, 7579; G. A. Molander and C. R. Harris, Chem. Rev., 1996, 96, 307.
8. For reviews, see G. A. Molander, Chem. Rev., 1992, 92, 29; D. P. Curran, T. L. Fevig, C. P. Jasperse and M. J. Totleben, Synlett, 1992, 943; J. Iqbal, B. Bhatia and N. K. Nayyar, Chem. Rev., 1994, 59, 519; P. I. Dalko, Tetrahedron, 1995, 51, 7579; G. A. Molander and C. R. Harris, Chem. Rev., 1996, 96, 307.
9. G. A. Molander and C. R. Harris, J. Am. Chem. Soc., 1996, 118, 4059; K. Takai, T. Ueda, N, Ikeda and T. Moriwake, J. Org. Chem., 1996, 61, 7990.
10. G. A. Molander and C. R. Harris, J. Am. Chem. Soc., 1996, 118, 4059; K. Takai, T. Ueda, N, Ikeda and T. Moriwake, J. Org. Chem., 1996, 61, 7990.
11. These skeletons are frequently found in Silphinene and related compounds; see F. Saitoh, M. Mori, K. Okamura and T. Date, Tetrahedron, 1995, 51, 4439; M. Franck-Neumann, M. Miesch and L. Gross, Tetrahedron Lett., 1991, 32, 2135; H.-Y. Lee, D.-I. Kim and S. Kim, Chem. Commun., 1996, 1539.
12. These skeletons are frequently found in Silphinene and related compounds; see F. Saitoh, M. Mori, K. Okamura and T. Date, Tetrahedron, 1995, 51, 4439; M. Franck-Neumann, M. Miesch and L. Gross, Tetrahedron Lett., 1991, 32, 2135; H.-Y. Lee, D.-I. Kim and S. Kim, Chem. Commun., 1996, 1539.
13. These skeletons are frequently found in Silphinene and related compounds; see F. Saitoh, M. Mori, K. Okamura and T. Date, Tetrahedron, 1995, 51, 4439; M. Franck-Neumann, M. Miesch and L. Gross, Tetrahedron Lett., 1991, 32, 2135; H.-Y. Lee, D.-I. Kim and S. Kim, Chem. Commun., 1996, 1539.
14. T. Shono, I. Nishiguchi and M. Sasaki, J. Am. Chem. Soc., 1978, 100, 4314.
15. Zinc was purchased from Nacalai Tesque Inc, and was used without activation: cf. K. Takai, T. Kakiuchi, Y. Kataoka and K. Utimoto, J. Org. Chem., 1994, 59, 2668; K. Takai, T. Kakiuchi and K. Utimoto, J Org. Chem., 1994, 59, 2671.
16. Zinc was purchased from Nacalai Tesque Inc, and was used without activation: cf. K. Takai, T. Kakiuchi, Y. Kataoka and K. Utimoto, J. Org. Chem., 1994, 59, 2668; K. Takai, T. Kakiuchi and K. Utimoto, J Org. Chem., 1994, 59, 2671.
17. Alternatively, the thermodynamically stable exo-CN isomer may be formed via isomerization. For related exo-selectivity, see W. Flitsch and P. Russkamp, Liebigs Ann. Chem., 1985, 1398.
18. D. L. Bogerand R. J. Mathvink, J. Org. Chem., 1992, 57, 1429; L. Chen, G. B. Gill and G. Pattenden, Tetrahdedron Lett., 1994, 35, 2593; L. Chen, G. B. Gill, G. Pattenden and H. Simonian, J. Chem. Soc., Perkin Trans. 1, 1996, 31; A. Batsanov, L. Chen, G. B. Gill and G. Pattenden, J. Chem. Soc., Perkin Trans. 1, 1996, 45.
19. D. L. Bogerand R. J. Mathvink, J. Org. Chem., 1992, 57, 1429; L. Chen, G. B. Gill and G. Pattenden, Tetrahdedron Lett., 1994, 35, 2593; L. Chen, G. B. Gill, G. Pattenden and H. Simonian, J. Chem. Soc., Perkin Trans. 1, 1996, 31; A. Batsanov, L. Chen, G. B. Gill and G. Pattenden, J. Chem. Soc., Perkin Trans. 1, 1996, 45.
20. D. L. Bogerand R. J. Mathvink, J. Org. Chem., 1992, 57, 1429; L. Chen, G. B. Gill and G. Pattenden, Tetrahdedron Lett., 1994, 35, 2593; L. Chen, G. B. Gill, G. Pattenden and H. Simonian, J. Chem. Soc., Perkin Trans. 1, 1996, 31; A. Batsanov, L. Chen, G. B. Gill and G. Pattenden, J. Chem. Soc., Perkin Trans. 1, 1996, 45.
21. D. L. Bogerand R. J. Mathvink, J. Org. Chem., 1992, 57, 1429; L. Chen, G. B. Gill and G. Pattenden, Tetrahdedron Lett., 1994, 35, 2593; L. Chen, G. B. Gill, G. Pattenden and H. Simonian, J. Chem. Soc., Perkin Trans. 1, 1996, 31; A. Batsanov, L. Chen, G. B. Gill and G. Pattenden, J. Chem. Soc., Perkin Trans. 1, 1996, 45.
22. cf. For radical/cationic reactions involving carbonylation, see I. Ryu and H. Alper, J. Am. Chem. Soc., 1993, 115, 7543; S. Tsunoi, I. Ryu and N. Sonoda, J. Am. Chem. Soc., 1994, 116, 5473; K. Okuro and H. Alper, J. Org. Chem., 1996, 61, 5312.
23. cf. For radical/cationic reactions involving carbonylation, see I. Ryu and H. Alper, J. Am. Chem. Soc., 1993, 115, 7543; S. Tsunoi, I. Ryu and N. Sonoda, J. Am. Chem. Soc., 1994, 116, 5473; K. Okuro and H. Alper, J. Org. Chem., 1996, 61, 5312.
24. cf. For radical/cationic reactions involving carbonylation, see I. Ryu and H. Alper, J. Am. Chem. Soc., 1993, 115, 7543; S. Tsunoi, I. Ryu and N. Sonoda, J. Am. Chem. Soc., 1994, 116, 5473; K. Okuro and H. Alper, J. Org. Chem., 1996, 61, 5312.