Silicon-assisted ring opening of donor-acceptor substituted cyclopropanes. An expedient entry to substituted dihydrofurans

Organic Letters

Volumn 3, Issue 17, 2001, Pages 2717-2718

  Yadav, Veejendra K ^a   Balamurugan, Rengarajan ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY KANPUR   (India)

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EID: 0008635079     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0163169     Document Type: Article

References (31)

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2. Ryu, I.; Hirai, A.; Suzuki, H.; Sonada, N.; Murai, S. J. Org. Chem. 1990, 55, 1409. Ryu, I.; Suzuki, H.; Murai, S.; Sonada, N. Organametallics 1987, 6, 212. Dubois, M. G.; Dunogues, J. J. Organomet. Chem. 1986, 309, 35. Dubois, M. G.; Calas, R. Can. J. Chem. 1981, 59, 802. Chan, T. H.; Fleming, I. Synthesis 1979, 761. Dubois, M. G.; Pillot, J.-P.; Dunogues, J.; Calas, R. J. Organomet. Chem. 1977, 124, 135.
3. Ryu, I.; Hirai, A.; Suzuki, H.; Sonada, N.; Murai, S. J. Org. Chem. 1990, 55, 1409. Ryu, I.; Suzuki, H.; Murai, S.; Sonada, N. Organametallics 1987, 6, 212. Dubois, M. G.; Dunogues, J. J. Organomet. Chem. 1986, 309, 35. Dubois, M. G.; Calas, R. Can. J. Chem. 1981, 59, 802. Chan, T. H.; Fleming, I. Synthesis 1979, 761. Dubois, M. G.; Pillot, J.-P.; Dunogues, J.; Calas, R. J. Organomet. Chem. 1977, 124, 135.
4. Ryu, I.; Hirai, A.; Suzuki, H.; Sonada, N.; Murai, S. J. Org. Chem. 1990, 55, 1409. Ryu, I.; Suzuki, H.; Murai, S.; Sonada, N. Organametallics 1987, 6, 212. Dubois, M. G.; Dunogues, J. J. Organomet. Chem. 1986, 309, 35. Dubois, M. G.; Calas, R. Can. J. Chem. 1981, 59, 802. Chan, T. H.; Fleming, I. Synthesis 1979, 761. Dubois, M. G.; Pillot, J.-P.; Dunogues, J.; Calas, R. J. Organomet. Chem. 1977, 124, 135.
5. Ryu, I.; Hirai, A.; Suzuki, H.; Sonada, N.; Murai, S. J. Org. Chem. 1990, 55, 1409. Ryu, I.; Suzuki, H.; Murai, S.; Sonada, N. Organametallics 1987, 6, 212. Dubois, M. G.; Dunogues, J. J. Organomet. Chem. 1986, 309, 35. Dubois, M. G.; Calas, R. Can. J. Chem. 1981, 59, 802. Chan, T. H.; Fleming, I. Synthesis 1979, 761. Dubois, M. G.; Pillot, J.-P.; Dunogues, J.; Calas, R. J. Organomet. Chem. 1977, 124, 135.
6. Ryu, I.; Hirai, A.; Suzuki, H.; Sonada, N.; Murai, S. J. Org. Chem. 1990, 55, 1409. Ryu, I.; Suzuki, H.; Murai, S.; Sonada, N. Organametallics 1987, 6, 212. Dubois, M. G.; Dunogues, J. J. Organomet. Chem. 1986, 309, 35. Dubois, M. G.; Calas, R. Can. J. Chem. 1981, 59, 802. Chan, T. H.; Fleming, I. Synthesis 1979, 761. Dubois, M. G.; Pillot, J.-P.; Dunogues, J.; Calas, R. J. Organomet. Chem. 1977, 124, 135.
7. Reissig, H.-U. In Topics in Current Chemistry; de Meijere, A., Ed.; Springer-Verlag: Berlin, Heidelberg, Germany, 1991; Vol. 144. pp 73-135.
8. Hirao, T.; Misu, D.; Agawa, T. J. Chem. Soc., Chem. Commun. 1986, 26. Reichelt, I.; Reissig, H.-U. Liebigs Ann. Chem. 1984, 828. Ochiai, M.; Sumi, K.; Fujita, E. Chem. Pharm. Bull. 1983, 31, 3931. Ochiai, M.; Sumi, K.; Fujita, E. Tetrahedron Lett. 1982, 23, 5419. Ochiai, M.; Sumi, K.; Fujita, E. Chem. Lett. 1982, 79.
9. Hirao, T.; Misu, D.; Agawa, T. J. Chem. Soc., Chem. Commun. 1986, 26. Reichelt, I.; Reissig, H.-U. Liebigs Ann. Chem. 1984, 828. Ochiai, M.; Sumi, K.; Fujita, E. Chem. Pharm. Bull. 1983, 31, 3931. Ochiai, M.; Sumi, K.; Fujita, E. Tetrahedron Lett. 1982, 23, 5419. Ochiai, M.; Sumi, K.; Fujita, E. Chem. Lett. 1982, 79.
10. Hirao, T.; Misu, D.; Agawa, T. J. Chem. Soc., Chem. Commun. 1986, 26. Reichelt, I.; Reissig, H.-U. Liebigs Ann. Chem. 1984, 828. Ochiai, M.; Sumi, K.; Fujita, E. Chem. Pharm. Bull. 1983, 31, 3931. Ochiai, M.; Sumi, K.; Fujita, E. Tetrahedron Lett. 1982, 23, 5419. Ochiai, M.; Sumi, K.; Fujita, E. Chem. Lett. 1982, 79.
11. Hirao, T.; Misu, D.; Agawa, T. J. Chem. Soc., Chem. Commun. 1986, 26. Reichelt, I.; Reissig, H.-U. Liebigs Ann. Chem. 1984, 828. Ochiai, M.; Sumi, K.; Fujita, E. Chem. Pharm. Bull. 1983, 31, 3931. Ochiai, M.; Sumi, K.; Fujita, E. Tetrahedron Lett. 1982, 23, 5419. Ochiai, M.; Sumi, K.; Fujita, E. Chem. Lett. 1982, 79.
12. Hirao, T.; Misu, D.; Agawa, T. J. Chem. Soc., Chem. Commun. 1986, 26. Reichelt, I.; Reissig, H.-U. Liebigs Ann. Chem. 1984, 828. Ochiai, M.; Sumi, K.; Fujita, E. Chem. Pharm. Bull. 1983, 31, 3931. Ochiai, M.; Sumi, K.; Fujita, E. Tetrahedron Lett. 1982, 23, 5419. Ochiai, M.; Sumi, K.; Fujita, E. Chem. Lett. 1982, 79.
13. Organ, M. G.; Dragan, V.; Miller, M.; Froese, R. D. J.; Goddard, J. D. J. Org. Chem. 2000, 65, 3666 and references therein. For an excellent review on the subject, see: Knolker, H.-J. J. Prakt. Chem. 1997, 339, 304.
14. Organ, M. G.; Dragan, V.; Miller, M.; Froese, R. D. J.; Goddard, J. D. J. Org. Chem. 2000, 65, 3666 and references therein. For an excellent review on the subject, see: Knolker, H.-J. J. Prakt. Chem. 1997, 339, 304.
15. For alternate syntheses of dihydrofurans, see: Antonioletti, R.; Righi, G.; Oliveri, L.; Bovicelli, P. Tetrahedron Lett. 2000, 41, 10127. Hwu, J. R.; Chen, C. N.; Shiao, S.-S. J. Org. Chem. 1995, 60, 856. Abdallah, H.; Gree, R.; Carrie, R. Tetrahedron 1985, 41, 4339. Also, see ref 9 of this paper.
16. For alternate syntheses of dihydrofurans, see: Antonioletti, R.; Righi, G.; Oliveri, L.; Bovicelli, P. Tetrahedron Lett. 2000, 41, 10127. Hwu, J. R.; Chen, C. N.; Shiao, S.-S. J. Org. Chem. 1995, 60, 856. Abdallah, H.; Gree, R.; Carrie, R. Tetrahedron 1985, 41, 4339. Also, see ref 9 of this paper.
17. For alternate syntheses of dihydrofurans, see: Antonioletti, R.; Righi, G.; Oliveri, L.; Bovicelli, P. Tetrahedron Lett. 2000, 41, 10127. Hwu, J. R.; Chen, C. N.; Shiao, S.-S. J. Org. Chem. 1995, 60, 856. Abdallah, H.; Gree, R.; Carrie, R. Tetrahedron 1985, 41, 4339. Also, see ref 9 of this paper.
18. The substituted cyclopropylmethylsilanes were prepared conveniently by a rhodium-catalyzed carbene insertion reaction of the corresponding diazo compound with allyl-tert-butyldiphenylsilane. 3c, 3d, and 3e were respectively 1.3:1, 1.4:1, and 1.7:1 mixtures of isomers.
19. 4. Removal of the solvents under reduced pressure furnished the crude product, which was purified by column chromatography (EtOAc/hexanes) to isolate 4a; yield 98 mg, 96%.
20. The structures of 4b and 4c were confirmed by comparing the spectral data available for similar known compounds reported in ref 5. The structures of 4a and 4d were confirmed by transforming them into 5-((tert-butyldiphenylsilyl)methyl)-γ-lactone by acid hydrolysis followed by dealkyl-decarboxylation and desulfonation, respectively.
21. Alonso, M. E.; Morales, A.; Chitty, A. W. J. Org. Chem. 1982, 47, 3747. Wenkert, E.; Alonso, M. E.; Buckwalter, B. L.; Sanchez, E. L. J. Am. Chem. Soc. 1983, 105, 2021.
22. Alonso, M. E.; Morales, A.; Chitty, A. W. J. Org. Chem. 1982, 47, 3747. Wenkert, E.; Alonso, M. E.; Buckwalter, B. L.; Sanchez, E. L. J. Am. Chem. Soc. 1983, 105, 2021.
23. For discussions on silyl-stabilized β-carbocations, see: Fleming, I. Frontier Orbitals and Organic Chemical Reactions; Wiley: London, 1976; p 81. Wierschke, S. G.; Chandrasekhar, J.; Jorgensen, W. L. J. Am. Chem. Soc. 1985, 107, 1496. Lambert, J. B.; Wang, G.-T.; Finzel, R. B.; Teramura, D. H. J. Am. Chem. Soc. 1987, 109, 7838. Lambert, J. B. Tetrahedron 1990, 46, 2677. Lambert, J. B.; Chelius, E. C. J. Am. Chem. Soc. 1990, 112, 8120. Green, A. J.; Kuan, Y.-L.; White, J. M. J. Org. Chem. 1995, 60, 2734. Gabelica, V.; Kresge, A. J. J. Am. Chem. Soc. 1996, 118, 3838. Chan, V. Y.; Clark, C. I.; Giordano, J.; Green, A. J.; Karalis, A.; White, J. M. J. Org. Chem. 1996, 61, 5227.
24. For discussions on silyl-stabilized β-carbocations, see: Fleming, I. Frontier Orbitals and Organic Chemical Reactions; Wiley: London, 1976; p 81. Wierschke, S. G.; Chandrasekhar, J.; Jorgensen, W. L. J. Am. Chem. Soc. 1985, 107, 1496. Lambert, J. B.; Wang, G.-T.; Finzel, R. B.; Teramura, D. H. J. Am. Chem. Soc. 1987, 109, 7838. Lambert, J. B. Tetrahedron 1990, 46, 2677. Lambert, J. B.; Chelius, E. C. J. Am. Chem. Soc. 1990, 112, 8120. Green, A. J.; Kuan, Y.-L.; White, J. M. J. Org. Chem. 1995, 60, 2734. Gabelica, V.; Kresge, A. J. J. Am. Chem. Soc. 1996, 118, 3838. Chan, V. Y.; Clark, C. I.; Giordano, J.; Green, A. J.; Karalis, A.; White, J. M. J. Org. Chem. 1996, 61, 5227.
25. For discussions on silyl-stabilized β-carbocations, see: Fleming, I. Frontier Orbitals and Organic Chemical Reactions; Wiley: London, 1976; p 81. Wierschke, S. G.; Chandrasekhar, J.; Jorgensen, W. L. J. Am. Chem. Soc. 1985, 107, 1496. Lambert, J. B.; Wang, G.-T.; Finzel, R. B.; Teramura, D. H. J. Am. Chem. Soc. 1987, 109, 7838. Lambert, J. B. Tetrahedron 1990, 46, 2677. Lambert, J. B.; Chelius, E. C. J. Am. Chem. Soc. 1990, 112, 8120. Green, A. J.; Kuan, Y.-L.; White, J. M. J. Org. Chem. 1995, 60, 2734. Gabelica, V.; Kresge, A. J. J. Am. Chem. Soc. 1996, 118, 3838. Chan, V. Y.; Clark, C. I.; Giordano, J.; Green, A. J.; Karalis, A.; White, J. M. J. Org. Chem. 1996, 61, 5227.
26. For discussions on silyl-stabilized β-carbocations, see: Fleming, I. Frontier Orbitals and Organic Chemical Reactions; Wiley: London, 1976; p 81. Wierschke, S. G.; Chandrasekhar, J.; Jorgensen, W. L. J. Am. Chem. Soc. 1985, 107, 1496. Lambert, J. B.; Wang, G.-T.; Finzel, R. B.; Teramura, D. H. J. Am. Chem. Soc. 1987, 109, 7838. Lambert, J. B. Tetrahedron 1990, 46, 2677. Lambert, J. B.; Chelius, E. C. J. Am. Chem. Soc. 1990, 112, 8120. Green, A. J.; Kuan, Y.-L.; White, J. M. J. Org. Chem. 1995, 60, 2734. Gabelica, V.; Kresge, A. J. J. Am. Chem. Soc. 1996, 118, 3838. Chan, V. Y.; Clark, C. I.; Giordano, J.; Green, A. J.; Karalis, A.; White, J. M. J. Org. Chem. 1996, 61, 5227.
27. For discussions on silyl-stabilized β-carbocations, see: Fleming, I. Frontier Orbitals and Organic Chemical Reactions; Wiley: London, 1976; p 81. Wierschke, S. G.; Chandrasekhar, J.; Jorgensen, W. L. J. Am. Chem. Soc. 1985, 107, 1496. Lambert, J. B.; Wang, G.-T.; Finzel, R. B.; Teramura, D. H. J. Am. Chem. Soc. 1987, 109, 7838. Lambert, J. B. Tetrahedron 1990, 46, 2677. Lambert, J. B.; Chelius, E. C. J. Am. Chem. Soc. 1990, 112, 8120. Green, A. J.; Kuan, Y.-L.; White, J. M. J. Org. Chem. 1995, 60, 2734. Gabelica, V.; Kresge, A. J. J. Am. Chem. Soc. 1996, 118, 3838. Chan, V. Y.; Clark, C. I.; Giordano, J.; Green, A. J.; Karalis, A.; White, J. M. J. Org. Chem. 1996, 61, 5227.
28. For discussions on silyl-stabilized β-carbocations, see: Fleming, I. Frontier Orbitals and Organic Chemical Reactions; Wiley: London, 1976; p 81. Wierschke, S. G.; Chandrasekhar, J.; Jorgensen, W. L. J. Am. Chem. Soc. 1985, 107, 1496. Lambert, J. B.; Wang, G.-T.; Finzel, R. B.; Teramura, D. H. J. Am. Chem. Soc. 1987, 109, 7838. Lambert, J. B. Tetrahedron 1990, 46, 2677. Lambert, J. B.; Chelius, E. C. J. Am. Chem. Soc. 1990, 112, 8120. Green, A. J.; Kuan, Y.-L.; White, J. M. J. Org. Chem. 1995, 60, 2734. Gabelica, V.; Kresge, A. J. J. Am. Chem. Soc. 1996, 118, 3838. Chan, V. Y.; Clark, C. I.; Giordano, J.; Green, A. J.; Karalis, A.; White, J. M. J. Org. Chem. 1996, 61, 5227.
29. For discussions on silyl-stabilized β-carbocations, see: Fleming, I. Frontier Orbitals and Organic Chemical Reactions; Wiley: London, 1976; p 81. Wierschke, S. G.; Chandrasekhar, J.; Jorgensen, W. L. J. Am. Chem. Soc. 1985, 107, 1496. Lambert, J. B.; Wang, G.-T.; Finzel, R. B.; Teramura, D. H. J. Am. Chem. Soc. 1987, 109, 7838. Lambert, J. B. Tetrahedron 1990, 46, 2677. Lambert, J. B.; Chelius, E. C. J. Am. Chem. Soc. 1990, 112, 8120. Green, A. J.; Kuan, Y.-L.; White, J. M. J. Org. Chem. 1995, 60, 2734. Gabelica, V.; Kresge, A. J. J. Am. Chem. Soc. 1996, 118, 3838. Chan, V. Y.; Clark, C. I.; Giordano, J.; Green, A. J.; Karalis, A.; White, J. M. J. Org. Chem. 1996, 61, 5227.
30. For discussions on silyl-stabilized β-carbocations, see: Fleming, I. Frontier Orbitals and Organic Chemical Reactions; Wiley: London, 1976; p 81. Wierschke, S. G.; Chandrasekhar, J.; Jorgensen, W. L. J. Am. Chem. Soc. 1985, 107, 1496. Lambert, J. B.; Wang, G.-T.; Finzel, R. B.; Teramura, D. H. J. Am. Chem. Soc. 1987, 109, 7838. Lambert, J. B. Tetrahedron 1990, 46, 2677. Lambert, J. B.; Chelius, E. C. J. Am. Chem. Soc. 1990, 112, 8120. Green, A. J.; Kuan, Y.-L.; White, J. M. J. Org. Chem. 1995, 60, 2734. Gabelica, V.; Kresge, A. J. J. Am. Chem. Soc. 1996, 118, 3838. Chan, V. Y.; Clark, C. I.; Giordano, J.; Green, A. J.; Karalis, A.; White, J. M. J. Org. Chem. 1996, 61, 5227.
31. Knolker, H.-J.; Jones, P. G.; Wanzl, G. Synlett 1998, 613.