Stereoselective Epoxidation of Acyclic Olefinic Carboxylic Acids via Iodolactonization

Journal of the American Chemical Society

Volumn 100, Issue 12, 1978, Pages 3950-3952

  Bartlett, Paul A ^a   Myerson, Joel ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001505949     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00480a061     Document Type: Article

References (35)

1. E.g., aldol condensation: H. O. House, D. S. Crumrine, A. Y. Teranishi, and H. D. Olmstead, J. Am. Chem. Soc., 95, 3310 (1975).
2. W. A. Kleschick, C. T. Buse, and C. H. Heathcock, Chem. Ber., 99, 247 (1977).
3. C. T. Buse and C. H. Heathcock, Chem. Ber., 99, 8109 (1977).
4. J. E. Dubois and P. Fellmann, Tetrahedron Lett., 1225 (1975).
5. Claisen rearrangement: W. Sucrow and W. Richter, Chem. Ber., 104, 3679 (1971).
6. S. R. Wilson and R. S. Myers, J. Org. Chem., 40, 3309 (1975).
7. R. E. Ireland, R. H. Mueller, and A. K. Willard, J. Am. Chem. Soc., 98, 2868 (1976).
8. 2-Asymmetric induction: (a). P. Chautemps and J. -L. Pierre, Tetrahedron, 32, 549 (1976).
9. S. Tanaka, H. Yamamoto, H. Nozaki, K. B. Sharpless, R. C. Michaelson, and J. D. Cutting, J. Am. Chem. Soc., 96, 5254 (1974).
10. 3-Asymmetric induction: P. A. Bartlett and K. K. Jernstedt, J. Am. Chem. Soc., 99, 4829 (1977).
11. J. Klein, J. Am. Chem. Soc., 81, 3611 (1959).
12. H. O. House, R. G. Carlson, H. Müller, A. W. Noltes, and C. D. Slater, J. Am. Chem. Soc., 84, 2614 (1962).
13. E. Wenkert, L. H. Liu, and D. B. R. Johnston, J. Org. Chem., 30, 722 (1965).
14. E. J. Corey, N. M. Weinshenker, T. K. Schaaf, and W. Huber, J. Am. Chem. Soc., 91, 5675 (1969).
15. E. J. Corey and R. Noyori, Tetrahedron Lett., 311 (1970).
16. H. O. House, D. G. Melillo, and F. J. Sauter, J. Org. Chem., 38, 741 (1973).
17. see also V. I. Staninets and E. A. Shilov, Russ. Chem. Rev., 272 (1971)., and references therein.
18. S. Terashima and S. -S. Jew, Tetrahedron Lett., 1005 (1977).
19. W. E. Barnett and W. H. Sohn, J. Chem. Soc., Chem. Commun., 472 (1972).; Tetrahedron Lett., 1777 (1972).
20. V. Jäger and H. J. Günther, Tetrahedron Lett., 2543 (1977).
21. K. Kondo, A. Negishi, and K. Matsui, Japanese Kokai, 77 05,708
22. Chem. Abstr., 86, 189231 (1977).
23. T. W. Campbell and W. G. Young, J. Am. Chem. Soc., 71, 296 (1949).
24. D. L. H. Williams, E. Bienvenüe-Goetz, and J, E. Dubois, J. Chem. Soc. B, 517 (1969).
25. C. V. Wilson, Org. React., 9, 332 (1957).
26. H. K. Hall, Jr., M. K. Brandt, and R. M. Mason, J. Am. Chem. Soc., 80, 6420 (1958).
27. L. do Amaral and S. C. Melo, J. Org. Chem., 38, 800 (1973).
28. N. L. Allinger, J. Am. Chem. Soc., 81, 232 (1959).
29. M. Julia and J. -M. Paris, Tetrahedron Lett., 4833 (1973).
30. P. A. Bartlett, F. R. Green III, and E. H. Rose, J. Am. Chem. Soc., in press.
31. R. A. Johnson, F. H. Lincoln, J. L. Thompson, E. G. Nidy, S. A. Mizsak, and U. Axen, J. Am. Chem. Soc., 99, 4184 (1977).
32. I. Tömösközi, G. Galambos, V. Simonidesz, and G. Kovács, Tetrahedron Lett., 2627 (1977).
33. N. Whittaker, J. Am. Chem. Soc., 2805 (1977).
34. G. T. Pearce, W. E. Gore, and R. M. Silverstein, J. Org. Chem., 41, 2797 (1975).
35. V. Prelog and W. Oppolzer, Helv. Chim. Acta, 56, 2279 (1973).