Intramolecular iodosilyletherization of alkenylsilanols with bis(2,4,6-trimethylpyridine)iodine(I) hexafluorophosphate

Tetrahedron Letters

Volumn 37, Issue 37, 1996, Pages 6781-6784

  Takaku, Koji ^a   Shinokubo, Hiroshi ^a   Oshima, Koichiro ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

SILANE DERIVATIVE;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030576965     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(96)01499-2     Document Type: Article

References (24)

1. 1. Fleming, I. Organosilicon Chemistry, in Comprehensive Organic Chemistry, Vol. 3, Pergamon Press: Oxford, 1979; Weber, W. P. Silicon Reagents for Organic Synthesis; Springer-Verlag: New York, 1983; Colvin, E. W. Silicon in Organic Synthesis; Butterworths: Boston, 1986; Colvin, E. W. Silicon Reagents in Organic Synthesis; Academic Press: London, 1988.
2. 1. Fleming, I. Organosilicon Chemistry, in Comprehensive Organic Chemistry, Vol. 3, Pergamon Press: Oxford, 1979; Weber, W. P. Silicon Reagents for Organic Synthesis; Springer-Verlag: New York, 1983; Colvin, E. W. Silicon in Organic Synthesis; Butterworths: Boston, 1986; Colvin, E. W. Silicon Reagents in Organic Synthesis; Academic Press: London, 1988.
3. 1. Fleming, I. Organosilicon Chemistry, in Comprehensive Organic Chemistry, Vol. 3, Pergamon Press: Oxford, 1979; Weber, W. P. Silicon Reagents for Organic Synthesis; Springer-Verlag: New York, 1983; Colvin, E. W. Silicon in Organic Synthesis; Butterworths: Boston, 1986; Colvin, E. W. Silicon Reagents in Organic Synthesis; Academic Press: London, 1988.
4. 1. Fleming, I. Organosilicon Chemistry, in Comprehensive Organic Chemistry, Vol. 3, Pergamon Press: Oxford, 1979; Weber, W. P. Silicon Reagents for Organic Synthesis; Springer-Verlag: New York, 1983; Colvin, E. W. Silicon in Organic Synthesis; Butterworths: Boston, 1986; Colvin, E. W. Silicon Reagents in Organic Synthesis; Academic Press: London, 1988.
5. 2. Trost, B. M.; Ito, N.; Greenspan, P. D. Tetrahedron Lett. 1993, 34, 1421-1424; Soderquist, J. A.; Vaquer, J.; Diaz, M. J.; Rane, A. M.; Bordwell, F. G.; Zhang, S. Tetrahedron Lett. 1996, 37, 2561-2564.
6. 2. Trost, B. M.; Ito, N.; Greenspan, P. D. Tetrahedron Lett. 1993, 34, 1421-1424; Soderquist, J. A.; Vaquer, J.; Diaz, M. J.; Rane, A. M.; Bordwell, F. G.; Zhang, S. Tetrahedron Lett. 1996, 37, 2561-2564.
7. 3. Chan, T. H.; Chen, L. M.; Wang, D.; Li, L. H. Can. J. Chem. 1993, 71, 60-67; Yamamoto, K.; Kawanami, Y.; Miyazawa, M. J. Chem. Soc., Chem. Commun. 1993, 436-437.
8. 3. Chan, T. H.; Chen, L. M.; Wang, D.; Li, L. H. Can. J. Chem. 1993, 71, 60-67; Yamamoto, K.; Kawanami, Y.; Miyazawa, M. J. Chem. Soc., Chem. Commun. 1993, 436-437.
9. 4. Alkenyl(dimethyl)silanols proved to be unstable and were readily converted into water and their disiloxanes in a few minutes. Thus, alkenyl(diphenyl)silanols, which were stable under the reaction conditions, were chosen as substrates. Two general procedures for the preparation of the representative silanols are shown below. (equation presented)
10. 5. Silyl groups reduce the basicity of heteroatoms to which they are directly bonded. Bassindale, A. R.; Taylor, P. G. in The Chemistry of Organic Silicon Compounds Part 1, Patai. S.; Rappoport. Z., Eds.; John Wiley & Sons: Chichester, 1989; Chapter 12, pp. 809-838.
11. 2 gave no trace of iodohydrin triphenylsilyl ether. In contrast, the reaction of cyclohexene with NIS and butanol provided 1-butoxy-2-iodo-cyclohexane in 41% yield under the same reaction conditions.
12. 7. Cambie, R. C.; Noall, W. I.; Potter, G. J.; Rutledge, P. S.; Woodgate, P. D. J. Chem. Soc., Perkin 1, 1977, 226-230.
13. 8. Harding, K. E.; Tiner, T. H. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Paquett, L. A., Eds.; Pergamon Press: New York, 1991; Vol. 4, Chapter 1.9, pp 363-421; Brunei, Y.; Rousseau, G. Synlett, 1995, 323-324; Evans, R. D.; Magee, J. W.; Schauble, J. H. Synthesis, 1988, 862-868.
14. 8. Harding, K. E.; Tiner, T. H. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Paquett, L. A., Eds.; Pergamon Press: New York, 1991; Vol. 4, Chapter 1.9, pp 363-421; Brunei, Y.; Rousseau, G. Synlett, 1995, 323-324; Evans, R. D.; Magee, J. W.; Schauble, J. H. Synthesis, 1988, 862-868.
15. 8. Harding, K. E.; Tiner, T. H. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Paquett, L. A., Eds.; Pergamon Press: New York, 1991; Vol. 4, Chapter 1.9, pp 363-421; Brunei, Y.; Rousseau, G. Synlett, 1995, 323-324; Evans, R. D.; Magee, J. W.; Schauble, J. H. Synthesis, 1988, 862-868.
16. 9. Simonot, B.; Rosseeau, G. J. Org. Chem. 1994, 59, 5912-5919. In general, bis(2,4,6-trimethylpyridine)iodine(I) hexafluorophosphate gave better yields of oxasilacycloalkane than NIS. For instance, treatment of 1h with bis(2,4,6-trimethylpyridine)iodine(I) hexafluorophosphate or NIS gave 2h in 83% or 32% yield, respectively.
17. 10. Baldwin, J. E. J. Chem. Soc., Chem. Commun. 1976, 734-738.
18. 6) 10.9, 30.0, 30.9, 31.6, 45.8, 76.5, 128.11, 128.12, 130.1, 130.2, 134.5, 134.9, 136.6, 137.2.
19. 12. Elimination of HI took place under the reaction conditions and isopropenyl-substituted products 2k and 21 were obtained instead of 1-iodo-1-methylethyl-substituted products.
20. 13. The reaction of 5-methyl-4-hexen-1-ol 4 with NIS gave a mixture of oxacyclopentane 5 and oxacyclohexane derivative 6 (5:6 = 13:87) in 99% combined yield. Intramolecular iodoetherization of (Z)-5-octen-1-ol 7 afforded 2-(1-iodopropyl)-1-oxacyclohexane 8 in 89% yield exclusively. (equation presented)
21. 14. Miura, K.; Ichinose, Y.; Nozaki, K.; Fugami, K.; Oshima, K.; Utimoto, K. Bull. Chem. Soc. Jpn., 1989, 62, 143-147.
22. 15. Tamao, K.; Kakui, T.; Akita, M.; Iwahara, T.; Kanatani, R.; Yoshida, J.; Kumada, M. Tetrahedron 1983, 39, 983-990; Tamao, K.; Ishida, N.; Kumada, M. J. Org. Chem. 1983, 48, 2120-2122; Fleming, I. Chemtracts. Org. Chem. 1996, 9, 1-64.
23. 15. Tamao, K.; Kakui, T.; Akita, M.; Iwahara, T.; Kanatani, R.; Yoshida, J.; Kumada, M. Tetrahedron 1983, 39, 983-990; Tamao, K.; Ishida, N.; Kumada, M. J. Org. Chem. 1983, 48, 2120-2122; Fleming, I. Chemtracts. Org. Chem. 1996, 9, 1-64.
24. 15. Tamao, K.; Kakui, T.; Akita, M.; Iwahara, T.; Kanatani, R.; Yoshida, J.; Kumada, M. Tetrahedron 1983, 39, 983-990; Tamao, K.; Ishida, N.; Kumada, M. J. Org. Chem. 1983, 48, 2120-2122; Fleming, I. Chemtracts. Org. Chem. 1996, 9, 1-64.