Chloromethanesulfonate as an efficient leaving group: Rearrangement of the carbon-carbon bond and conversion of alcohols into azides and nitriles

Synthesis

Volumn , Issue 8, 1999, Pages 1373-1385

  Shimizu, Takeshi ^a   Ohzeki, Tomoya ^a   Hiramoto, Katsuya ^a   Hori, Nobuyuki ^a   Nakata, Tadashi ^a  

^a INST OF PHYS AND CHEMICAL RESEARCH   (Japan)

Author keywords

Azide; Chloromethanesulfonate; Methyl migration; Nitrile; Rearrangement

Indexed keywords

ALCOHOL DERIVATIVE; AZIDE; CHLOROMETHANESULFONIC ACID; DIOXANE; MESYLIC ACID DERIVATIVE; NITRILE; SODIUM CYANIDE; UNCLASSIFIED DRUG; ZINC ACETATE;

ARTICLE; CHEMICAL BOND; REACTION ANALYSIS; STEREOSPECIFICITY; SYNTHESIS; TEMPERATURE;

EID: 0032871432     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1999-3541     Document Type: Article

References (24)

1. Shimizu, T.; Hiranuma, S.; Nakata, T. Tetrahedron Lett. 1996, 37, 6145.
2. Nakata, T.; Nomura, S.; Matsukura, H. Tetrahedron Lett. 1996, 37, 213.
3. Hori, N.; Nagasawa, K.; Shimizu, T.; Nakata, T. Tetrahedron Lett. 1999, 40, 2145.
4. Morimoto, M.; Matsukura, H.; Nakata, T. Tetrahedron Lett. 1996, 37, 6356.
5. Hoffmann, J. J.; Punnapayak, S. D.; Jold, S. D.; Bates, R. B.; Camou, F. A. J. Nat. Prod. 1988, 51, 125.
6. 4; (d) McCl, pyridine (37% overall yield).
7. Shoppee, C. W.; Johnston, G. A. R. J. Chem. Soc. 1961, 3261.
8. Manchand, P. S.; Blount, J. F. Tetrahedron Lett. 1976, 2489.
9. Ying, B. -P.; Peiser, G.; Ji, Y. -Y.; Mathias, K.; Tutko, D.; Hwang, Y. -S Photochemistry 1995, 38, 909.
10. 3): δ = 0.82 (s, 3H), 0.92 (s, 9H), 0.95 (s, 3H), 1.03 (s, 9H), 1.18 (s, 3H), 1.72 (br s, 3H), 3.38 (br s, 1H), 3.66-3.77 (m, 2H), 5.47 (br s, 1H).
11. 3): δ = 0.72 (s, 3H), 0.98 (d, J = 6.3 Hz, 3H), 1.01 (s, 3H), 3.67 (s, 3H), 4.04 (dd, J = 2.8, 2.8 Hz, 1H).
12. Shimagaki, M.; Fujieda, Y.; Kimura, T.; Nakata, T. Tetrahedron Lett. 1995, 36, 719 and references therein.
13. 3): δ = 0.72 (s, 3H), 0.86 (d, J = 6.6 Hz, 6H), 0.89 (d, J = 6.6 Hz, 3H), 0.90 (s, 3H), 5.18 (dd, J = 9.7, 2.6 Hz, 1H), 5.38 (br s, 1H), 5.52 (dd, J = 9.7, 1.0 Hz, 1H). 36c was determined by NMR spectra to be identical to commercial sample of cholesta-3,5-diene.
14. Wendler, N.L. In Molecular Rearrangement, Vol II; De Mayo, P., Ed.; Interscience, New York, 1963; p 1075.
15. 3): δ = 20.1, 29.6, 33.2, 69.1, 73.1, 126.2, 126.6, 127.6, 128.8, 137.6, 139.1. * Nicos, A.; Shao-Po, L. Tetrahedron Lett. 1995, 36, 2393.
16. Scriven, E. F. V.; Turnbull, K. Chem. Rev. 1988, 88, 297. Hughes, D. L. Org. React. 1992, 42, 335.
17. Scriven, E. F. V.; Turnbull, K. Chem. Rev. 1988, 88, 297. Hughes, D. L. Org. React. 1992, 42, 335.
18. Henbest, H. B.; Jackson, W.R. J. Chem. Soc. 1962, 954. Loibner, H.; Zbiral, E. Helv. Chim. Acta 1977, 60, 417.
19. Henbest, H. B.; Jackson, W.R. J. Chem. Soc. 1962, 954. Loibner, H.; Zbiral, E. Helv. Chim. Acta 1977, 60, 417.
20. 3): δ = 11.2, 23.2, 26.4, 27.3, 29.9, 30.7, 36.8, 38.9, 43.3, 44.0, 50.1, 55.2, 111.4, 113.7, 126.2, 132.5, 137.8, 157.3.
21. Bose, A. K.; Kistner, J. F.; Farber, L. J. Org. Chem. 1962, 27, 2925. Loibner, H.; Zbiral, E. Helv. Chim. Acta 1976, 59, 2100.
22. Bose, A. K.; Kistner, J. F.; Farber, L. J. Org. Chem. 1962, 27, 2925. Loibner, H.; Zbiral, E. Helv. Chim. Acta 1976, 59, 2100.
23. Alcohol 56 was provided by Dr. T. Suenaga in this laboratory.
24. Alcohol 59 was prepared from (2R,3S,6S)-6-[(4R)-2,2-dimethyl-1,3-dioxoran-4-yI]-2-hydroxymethyl-6- methyltetrahydro-2H-pyran-3-oI (Nakata, T.; Nomura, S.; Matsukura, H.; Morimoto, M. Tetrahedron Lett. 1996, 37, 217.) in nine steps. Details for the preparation will be reported elsewhere.