Diastereoselective singlet oxygen ene reaction (Schenck reaction) and diastereoselective epoxidations of heteroatom-substituted acyclic chiral olefins: A mechanistic comparison

Journal of the American Chemical Society

Volumn 118, Issue 8, 1996, Pages 1899-1905

  Adam, Waldemar ^a   Brünker, Hans Günter ^a   Kumar, A Sampath ^a   Peters, Eva Maria ^b   Peters, Karl ^b   Schneider, Uwe ^a   Von Schnering, Hans Georg ^b  

^a UNIVERSITY OF WÜRZBURG   (Germany)

^b MAX PLANCK INSTITUT FÜR FESTKÖRPERFORSCHUNG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

HYDROPEROXIDE;

ARTICLE; DRUG SYNTHESIS; PHOTOCHEMISTRY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0029872958     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9530230     Document Type: Article

References (69)

1. Undergraduate research participant. Spring 1994.
2. Schenck, G. O.; Eggert. H.; Denk. W. Liebigs Ann. Chem. 1953, 584, 177-198.
3. Matsumoto, M. In Singlet Oxygen; Frimer, A. A., Ed.; CRC Press: Boca Raton, FL, 1985; Vol II, pp 212-272.
4. (a) Orfanopoulos, M.; Grdina, M. B., Stephenson. L. M. J. Am. Chem. Soc. 1979. 101, 275-276.
5. (b) Schulte-Ehe. K. H.; Rautenstrauch, V. J. Am. Chem. Soc: 1980, 102, 1738-1740.
6. (a) Ensley, H. E.; Carr, R. V. C: Martin. R. S , Pierce. T. E. J. Am. Chem. Soc. 1980, 102, 2836-2838.
7. (b) Orfanopoulos, M.; Foote. C. S. Tetrahedron Lett. 1985. 26. 5991-5994.
8. (c) Adam. W.; Griesbeck, A. Angew. Chem., Int. Ed. Engl. 1985, 24, 1070-1071.
9. (d) Akasaka. T., Takeuchi, K.; Ando, W. Tetrahedron Lett. 1987. 28. 6633-6636.
10. (e) Akasaka, T.; Misawa, Y.; Goto, M.; Ando, W. Tetrahedron 1989.45. 6657-6666.
11. (f) Clennan, E. L., Chen, X., Koola, J. J. J. Am. Chem. Soc 1990. 112. 5193-5199.
12. (g) Adam, W.; Brunker, H.-G., Nestler, B. Tetrahedron Lett. 1991. 32, 1957-1960.
13. Orfanopoulos, M.; Stratakis, M.: Elemes, Y. J. Am. Chem. Soc. 1990, 112. 6417-6419.
14. (a) Fristad, W. E., Bailey, T. R.; Paquette, L. A.; Gleiter, R.: Bohm, M. C J Am. Chem. Soc: 1979. 101. 4420-4423.
15. (b) Fnstad, W. E., Bailey, T. R.: Raquette, L. A. J. Org. Chem. 1980, 45. 3028-3037.
16. (c) Adam. W.: Richter, M. Tetrahedron Lett. 1992. 33. 3461-3464.
17. Adam, W., Klug, P. J. Org. Chem. 1993. 58. 3416-3420.
18. (a) Schenk, G. O.; Neumüller, O.-A.: Eisfeld, W. Liebigs Ann. Chem. 1958, 618, 202-210.
19. (b) Furutachi, N.; Nakauaira. Y.; Nakanishi, K. J. Chem. Soc., Chem. Commun. 1968, 1625-1626.
20. (c) Paquette, L. A.; Liao, C. C.; Liotta, D. C.; Fristad. W. E. J. Am. Chem. Soc. 1976. 98. 6412-6413.
21. (d) Lin, H.-S.; Paquette, L. A. Synth. Commun. 1986, 16. 1275-1283.
22. (e) Linker, T.; Fröhlich, L. Angew. Chem., Im. Ed. Engl. 1994, 33, 1971-1972.
23. Adam. W.; Catalani. L. H.: Griesbeck. A. J. Org. Chem. 1986, 51, 5494-5496.
24. (a) Adam, W.: Nestler, B. Liebigs Ann. Chem. 1990. 1051-1053.
25. (b) Kxopf, H.; Reichwaldt, R. J. Chem. Res. 1987. 412-413.
26. (a) Adam, W.; Nestler. B. J. Am. Chem. Soc. 1992. 114. 6549-6550.
27. (b) Adam, W. Nestler, B. J. Am. Chem. Soc 1993, 115. 5041 -5049.
28. (a) Adam, W.: Brünker, U-G. J. Am. Chem. Soc. 1993, 115, 3008-3009.
29. (b) Brünker, H.-G.; Adam, W. J. Am. Chem. Soc. 1995. 117. 3976-3982.
30. (a) Rao, A. S. Comprehensive Organic Synthesis, Ley, S. V., Ed.; Pergamon Press: Oxford, U.K., 1991: Vol. 7, pp 357-387.
31. (b) Sharpless, K. B.; Verhoeven, T. R. Aldrichim. Acta 1979, 12. 63-74.
32. (c) Henbest, H. B.; Wilson, R. A. L. J. Chem. Soc. 1957, 1958-1965.
33. (d) Berti, G. Top. Siereochem. 1973, 7, 93-251.
34. (e) Rao, A. S.; Paknikar, S. K.; Kirtane, J. G. Tetrahedron 1983, 39, 2323-2367.
35. (f) Rossiter, B. E.; Verhoeven, T. R.; Sharpless, K. B. Tetrahedron Lett. 1979, 4733-4736.
36. (g) Narula, A. S. Tetrahedron Lett. 1983, 24, 5421-5424.
37. (h) Hoveyda, A. H.; Evans, D. A.; Fu, G. C. Chem. Rev. 1993, 93, 1307-1370.
38. (a) Fleming, I., Sarkar, A. K.; Thomas, A. P. J. Chem. Soc., Chem. Commun. 1987. 157-159.
39. (b) Vedejs, E.; McClure, C. K. J. Am. Chem. Soc. 1986, 108, 1094-1096.
40. (c) Hayashi, T.: Okamoto. Y.; Kabeta, K.: Hagihara, T.; Kumada, M. J. Org. Chem. 1984,49,4224-4226.
41. (d) Nagase, T.; Kawashima, T.; Inamoto. N. Chem. Lett. 1985, 1655-1658.
42. (e) Clayden, J.; Collingion. E. W.: Egert, E.; McElroy. A. B.: Warren. S. J. Chem. Soc., Perkin. Trans. 1 1994. 2801-2810.
43. (f) Kocienski, P. J. Chem. Soc., Perkin Trans, 1 1983, 945-948.
44. (a) Nemes, C., Lévai. A.: Patonay, T., Tóth, G., Boros. S., Halász. J.; Adam, W.; Golsch. D. J. Org. Chem. 1994. 59. 900-905.
45. (b) Adam, W . Hadjiarapoglou, L. Top. Curr. Chem. 1993, 164. 45-62.
46. (c) Abou-Elzahab, M., Adam. W., Saha-Möller, C. R. Liebigs Ann. Chem. 1991. 445-50.
47. (d) Adam, W : Prechtl. F: Richter. M. J.: Smerz. A. K. Tetrahedron Lett. 1993. 34. 8427-8430
48. (e) Asensio, G.; Mello. R : Boix-Bemadini, C.; González-Nunez, M. E.; Castellano. G. J Org. Chem. 1995, 60, 3692-3699.
49. (f) Murray, R. W.; Singh, M. Williams. B L.; Moncrieff. H. M. Tetrahedron Lett. 1995. 36. 2437-2440
50. (g) Adam, W.: Smerz. A K. J. Chem. Soc.. Chem. Commun., submitted.
51. Tang, R.: Mislow. K. J. Am. Chem. Soc. 1970, 92. 2100-2104.
52. Prat, D.; Delpech, B.; Lett, R. Tetrahedron Lett. 1986. 27. 711-714.
53. Heathcock, C. H.; Finkelstein, B. L.; Jarvi, E. T.; Radel, P. A, Hadley, C. R. J. Org. Chem. 1988, 53, 1922-1942.
54. (a) Carretero, J. C.; Garcia Ruano, J. L.; Martinez, M. C.; Rodriguez, J. H.; Alcudia. F. Tetrahedron 1985. 41, 2419-2433.
55. (b) Brunet, E., Garcia Ruano, J L.; Martinez, M. C,; Rodriguez, J. H.; Alcudia, F. Tetrahedron 1984. 40. 2023-2034.
56. Sauleau, J. Bull. Soc. Chim. Fr. 1978. 474-480.
57. (a) Roush. W. R : Straub. J. A : Brown. R. S. J. Org. Chem. 1987. 52. 5127-5136.
58. (b) Luly. J. R.: Dellana. J. F . Planner. J. J.: Soderquist. J. L-. Yi. N. J. Org. Chem. 1987. 52. 1487- 1492.
59. (c) Hauser. F. M.: Ellenberger, S. R.: Glusker. J. P.: Smart, C. J.; Carrell. H. L. J. Org. Chem. 1986. 51. 50-57.
60. Hofmann. R. W Chem. Rev. 1989. 89, 1841-1860.
61. (a) Bartlett, P. D. Rec. Chem. Prog. 1950. 11. 47-51.
62. (b) Hanzlik, R. P.: Shearer, G- O. J. Am. Chem. Soc. 1975. 97. 5231-5233
63. (c) Plesnicar, B., Tasevski, M., Azman, A. J. Am. Chem. Soc. 1978, 100, 743-746.
64. (d) Woods. K. W.: Beak. P. J. Am. Chem. Soc. 1991. 113. 6281-6283.
65. (d) Bach. R. D., Owensby, A L.: Gonzales. C.: Schlegel, H B.: McDouall. J. J. W. J. Am Chem. Soc. 1991. 113. 2338-2341.
66. Murray, R. W,; Gu. D. J. Chem. Soc., Perkin Trans. 2 1993. 2203-2307.
67. Bach. R. D-. Owensbv A. L . Andres. J. L., Schlegel. H. B. J. Am. Chem. Soc. 1991. 113. 7031-7033.
68. Adam, W.: Curei, R : González Nuñez. M. E.: Mello, R, J. Am. Chem Soc. 1991. 113. 7654-7658.
69. Fujita, M. Ishizuka. H.: Oguri, K. Tetrahedron Lett. 1991. 32, 6355-6358.