Selective Transformations of 2,3-Epoxy Alcohols and Related Derivatives. Strategies for Nucleophilic Attack at Carbon-3 or Carbon-2

Journal of Organic Chemistry

Volumn 50, Issue 26, 1985, Pages 5696-5704

  Behrens, Carl H ^a   Sharpless, K Barry ^a  

^a MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0344882737     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00350a051     Document Type: Article

References (37)

1. See: Behrens, C. H.; Ko, S. Y.; Sharpless, K. B.; Walker, F. J. J. Org. Chem., preceding paper in this issue and references cited there in.
2. (a) Minami, N.; Ko, S. S.; Kishi, Y. J. Am. Chem. Soc. 1982, 104, 1109. (b) Ma, P.; Martin, V. S.; Masamune, S.; Sharpless, K. B.; Viti, S. M. J. Org. Chem. 1982, 47, 1378,. (c) Finan, J. M.; Kishi, Y. Tetrahedron Lett. 1982, 23, 2719. (d) Viti, S. M. Tetrahedron Lett. 1982, 23, 4541. (e) Nicolaou, K. C.; Venishi, J. J. Chem. Soc., Chem. Commun. 1982,1292. (f) Mubarak, A. M.; Brown, D. M. J. Chem. Soc., Perkin Trans. 1 1982, 809. (g) Takano, S.; Kasahara, C.; Ogasawara, K. Chem. Lett. 1983,175.
3. (a) Corey, E. J.; Hopkins, P. B.; Munroe, J. E.; Marfat, A.; Hashimoto, S. J. Am. Chem. Soc. 1980, 102, 7986. (b) Roush, W. R.; Brown, R. J. J. Org. Chem. 1982, 47, 1371. (c) Roush, W. R.; Brown, R. J.; DiMare, M. J. Org. Chem. 1983, 48, 5083. (d) Roush, W. R.; Brown, R. J. J. Org. Chem. 1983, 48, 5093. (e) Roush, W. R.; Adam, M. A.; Hagadorn, S. M., unpublished results. (f) Sorokin, M. F.; Shode, L. G.; Nogteva, S. I. Tr. Mosk. Khim.-Tekhnol. Inst. im. D. I. Mendeleeva 1980,110, 132; Chem. Abstr. 1982, 96, 121959k.
4. Weissenberg, M.; Krinsky, P.; Glotter, E. J. Chem. Soc., Perkin Trans. 1 1978, 565.
5. Danishefsky, S.; Tsai, M.-Y.; Kitahara, T. J. Org. Chem. 1977, 42, 394 and references cited there in.
6. Sharpless, K. B.; Behrens, C. H.; Katsuki, T.; Lee, A. W. M.; Martin, V. S.; Takatani, M.; Viti, S. M.; Walker, F. J.; Woodard, S. S. Pure Appl. Chem. 1983, 55, 589.
7. Kishi, Y. Aldrichimica Acta 1980, 13, 23.
8. (a) Hartman, B. C.; Livinghouse, T.; Rickborn, B. J. Org. Chem. 1973, 38, 4346. (b) Nagaoka, H.; Rutsch, W.; Schmid, G.; Iio, H.; Johnson, M. R.; Kishi, Y. J. Am. Chem. Soc. 1980, 102, 7962. (c) Nagaoka, H.; Kishi, Y. Tetrahedron 1981, 37, 3873. (d) Hayami, H.; Sato, M.; Kanemoto, S.; Morizawa, Y.,; Oshima, K.; Nozaki, H. J. Am. Chem. Soc. 1983, 105, 4491. (e) Lipshutz, B. H.; Kozlowski, J.; Wilhelm, R. S. J. Am. Chem. Soc. 1982, 104, 2305.
9. (a) Roush, W. R.; Adam, M. A.; Peseckis, S. M. Tetrahedron Lett. 1983, 24, 1377. (b) McWhorter, Jr., W. W.; Kang, S. H.; Kishi, Y. Tetrahedron Lett. 1983, 24, 2243. (c) Fuganti, C.; Grasselli, P.; Servi, S.; Zirotti, C. Tetrahedron Lett. 1982, 23, 4269.
10. Suzuki, T.; Saimoto, H.; Tomioka, H.; Oshima, K. Tetrahedron Lett. 1982, 23, 3597.
11. Pfaltz, A.; Mattenberger, A. Angew. Chem., Int. Ed. Engl. 1982, 21, 71.
12. Matthews, R. S.; Mihelich, E. D.; McGowan, L. S.; Daniels, K. J. Org. Chem. 1983, 48, 409.
13. (a) Tucker, H. J. Org. Chem. 1979, 44, 2943. (b) Shtacher, G.; Rubinstein, R.; Somani, P. J. Med. Chem. 1978, 21, 678.
14. Caron, M.; Sharpless, K. B., unpublished results. See also ref 25. (15) Guthrie, R. D.; Murphy, D. J. Chem. Soc. 1963, 5288.
15. 3, MeOH, reflux) is effective with 2,3-epoxy amides (vide infra) but much less effective with 2,3-epoxy alcohols.
16. 3(δ 3.3—3-9), and RR'CHOAc (δ 1.9-2.2) of the peracetylated products were found to be particularly useful.
17. (formula omitted)
18. 1H NMR spectrum of the unpurified diol product mixture and in the unpurified product mixture after peracetylation with pyridine and acetic anhydride. The signals of the hydroxyl proton (δ1.7-2.9) of the diol products and the signals corresponding to RR'CHOAc (δ 5–6), RR'CHSPh (δ 2–3), and RR'CHOAc (δ 1.7-2.2) of the peracetylated products were found to be particularly useful.
19. VanderWerf, C. A.; Heisler, R. Y.; McEwen, W. E. J. Am. Chem. Soc. 1954, 76, 1231.
20. McBee, E. T.; Hathaway, C. E.; Roberts, C. W. J. Am. Chem. Soc. 1956, 78, 4053.
21. Bordwell, F. G.; Brannen, Jr., W. T. J. Am. Chem. Soc. 1964, 86, 4645.
22. Hine, J.; Brader, Jr., W. H. J. Am. Chem. Soc. 1953, 75, 3964.
23. Williams, N. R. In “Advances in Carbohydrate Chemistry and Biochemistry”; Tipson, R. S., Horton, D., Eds.; Academic Press: New York, 1970; Vol. 25, p 109. (28) Fourneau, J. P.; Chantalou, S. Bull. Soc. Chim. Fr. 1945,12, 845.
24. (a) Corey, E. J.; Marfat, A.; Goto, G. J. Am. Chem. Soc. 1980,102, 6607. (b) Corey, E. J.; Marfat, A.; Monroe, J.; Kim, K. S.; Kaplin, P. B.; Brion, F. Tetrahedron Lett. 1981, 22, 1077. (c) Rossiter, B. E.; Katsuki, T.; Sharpless, K. B. J. Am. Chem. Soc. 1981, 103, 464. (d) Mills, L. S.; North, P. C. Tetrahedron Lett. 1983, 24, 409.
25. Tsunoda, T.; Suzuki, M.; Noyori, R. Tetrahedron Lett. 1980, 21, 1357.
26. 4NBr (10 equiv) in MeOH (0.1 M solution) yielded the bromohydrindimethyl acetal, which then, was converted to the desired epoxy acetal by treatment with a base. This is clearly the best route to homochiral epoxy acetals provided the rest of the molecule can tolerate the strong acidity of the first step. Gao, Y.; Sharpless, K. B., unpublished results. (formula omitted) (32) Foster, A. B. In “The Carbohydrates”Pigman, W., Horton, D., Eds.; Academic Press: New York, 1972; Vol. 1A, p 391.
27. Liwschitz, Y.; Rabinsohn, Y.; Perera, D.J. Chem. Soc. 1962, 1116.
28. (a) Kamandi, E.; Frahm, A. W.; Zymalkowski, F. Arch. Pharm. (Weinheim, Ger.) 1974, 307, 871. (b) Kamandi, E.; Frahm, A. W.; Zymalkowski, F. Arch. Pharm. (Weinheim, Ger.) 1975, 308,135. (c) Tack, J. W.; Lehmann, J.; Zymalkowski, F. Arch. Pharm. (Weinheim, Ger.) 1979, 312, 138. (d) Schonen, B.; Zymalkowski, F. Arch. Pharm. (Weinheim, Ger.) 1981, 314, 464. (e) Elker, A.; Lehmann, J.; Zymalkowski, F. Arch. Pharm. (Weinheim, Ger.) 1979, 312, 26.
29. (a) Kato, K.; Saino, T.; Nishizawa, R.; Takita, T.; Umezawa, H. J. Chem. Soc., Perkin Trans. 1 1980, 1618. (b) Takeuchi, S.; Ohgo, Y. Bull. Chem. Soc. Jpn. 1981, 54, 2136.
30. See numerous references to Martynov's work in Parker, R. E.; Isaacs, N. S. Chem. Rev. 1959, 59, 737.
31. Walborsky, H. M.; Baum, M. E. J. Am. Chem. Soc. 1958, 80, 187.
32. Carlsen, P. H. J.; Katsuki, T.; Martin, V. S.; Sharpless, K. B. J. Org. Chem. 1981, 46, 3936.
33. (a) Arnett, E. M. In “Progress in Physical and Organic Chemistry”Cohen, S. G., Streitweiser, Jr., A., Taft, R. W., Eds.; Interscience: New York, 1963; Vol. 1, p 223. (b) Drago, R. S.; Wayland, B. B. J. Am. Chem. Soc. 1965, 87, 3571. (40) The reaction of sodium trans-2,3-epoxy-5-phenylpentanoate 5-phenylpentanoate with benzenethiolate affords the C-2 ring-opened product with a regioselectivity of >20:1. Takatani, M.; Sharpless, K. B., unpublished results.
34. Still, W. C.; Kahn, M.; Mitra, A. J. Org. Chem. 1978, 43, 2923.
35. Micovic, V. M.; Mihailovic, M. L. J. Org. Chem. 1953, 18, 1190.
36. Chong, J. M.; Sharpless, K. B. J. Org. Chem. 1985, 50, 1560.
37. trans-2,3-Epoxy acids have been found to react with organocuprates selectively at C-2, whereas cis-2,3-epoxy acids react with the same reagents selectively at C-3 (Chong, J. M.; Sharpless, K. B. Tetrahedron Lett., in press). These cuprate openings of glycidic acids are not necessarily related to the chelation phenomena described in ref 25 and 43 and are only mentioned here for the sake of readers who are generally interested in the reaction of epoxy alcohols and their derivatives.