Long-Range Electrostatic Effects in Synthesis: Dipole-Controlled Nucleophilic Addition to a Naphthoquinone Acetal in Model Studies toward Diepoxin σ

Angewandte Chemie (International Edition in English)

Volumn 36, Issue 7, 1997, Pages 764-767

  Wipf, Peter ^a   Jung, Jae Kyu ^a  

^a UNIVERSITY OF PITTSBURGH   (United States)

Author keywords

Asymmetric synthesis; Chiral auxiliaries; Electrostatic effects; Nucleophilic additions; Solvent effects

Indexed keywords

EID: 0030756274     PISSN: 05700833     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.199707641     Document Type: Article

References (46)

1. D. J. Cram, D. J., F. A. A. Elhafez, J. Am. Chem. Soc. 1952. 74, 5828-5835.
2. V. Prelog, Helv, Chim. Acta 1953, 36, 308-319.
3. J. W. Cornforth, R. H. Cornforth, K. K. Mathew, J. Chem. Soc. 1959, 112-127.
4. a) M. Cherest, H. Felkin, N. Prudent, Tetrahedron Lett. 1968, 2199-2204;
5. b) N. T. Anh, O. Eisenstein, Nouv. J. Chim. 1977, 1, 61-70.
6. A. S. Cieplak, J. Am. Chem. Soc. 1981, 103, 4540-4552.
7. For a recent review, see B. W Gung, Tetrahedron 1996, 52, 5263-5301.
8. a) W. G. Dauben, G. J. Fonken, D. S. Noyce, J. Am. Chem. Soc. 1956, 78, 2579-2582;
9. b) J.-C. Richer. J. Org. Chem. 1965, 30, 324-325;
10. c) G. J. Karabatsos. J. Am. Chem. Soc. 1967, 89, 1367-1371;
11. d) J. Klein, Tetrahedron 1974, 30, 3349-3353;
12. e) M. R. Giddings, J. Hudec, Can. J. Chem. 1981, 59, 459-467;
13. f) E. M. Burgess, C. L. Liotta. J. Org. Chem. 1981, 46, 1703-1708;
14. g) L. A. Paquette, L.-H. Hsu, J. C. Gallucci, J. D. Korp, I. Bemal, T. M. Kravetz, S. J. Hatheway, J. Am. Chem. Soc. 1984, 106, 5743-5744;
15. h) S. S. Wong, M. N. Paddon-Row, J. Chem. Soc. Chem. Commun. 1990, 456-458;
16. i) H. Li, W. J. le Noble. Recl. Trav. Chim. Pays-Bas 1992, 111, 199-210;
17. j) Y-D, Wu, K. N. Houk, M. N. Paddon-Row, Angew. Chem. 1992. 104, 1087-1089; Angew. Chem. Int. Ed. Engl. 1992, 31, 1019-1021;
18. j) Y-D, Wu, K. N. Houk, M. N. Paddon-Row, Angew. Chem. 1992. 104, 1087-1089; Angew. Chem. Int. Ed. Engl. 1992, 31, 1019-1021;
19. k) B. Ganguly, J. Chandrasekhar, F. A. Khan, G. Mehta, J. Org. Chem, 1993, 58, 1734-1739;
20. l) X. L. Huang, J. J. Dannenberg, J. Am. Chem. Soc. 1993, 115, 6017-6024;
21. m) G. Frenking, K. F. Kohler, M. T. Reetz. Angew. Chem. 1991, 103, 1167-1670; Angew. Chem. Int. Ed. Eugl. 1991, 30, 1146-1149;
22. m) G. Frenking, K. F. Kohler, M. T. Reetz. Angew. Chem. 1991, 103, 1167-1670; Angew. Chem. Int. Ed. Eugl. 1991, 30, 1146-1149;
23. n) J. M. Coxon, K. N. Houk, R. T. Luibrand, J. Org. Chem. 1995, 60, 438-427;
24. o) N. T. Anh, F. Maurel, J.-M. Lefour, New. J. Chem. 1995, 19, 353-364;
25. p) M. Kaselj, J. L. Adcock, H. Luo, H. Zhang, H. Li, W. J. le Noble, J. Am. Chem. Soc. 1995, 117, 7088-91.
26. q) E. M. Gonikberg, W. J. le Noble, J. Org. Chem. 1995, 60, 7751-7755;
27. r)T. Sato, M. Kido, J. Otera, Angew. Chem. 1995, 107, 2459-2461; Angew. Chem. Int. Ed. Engl. 1995, 34, 2254-2256.
28. r)T. Sato, M. Kido, J. Otera, Angew. Chem. 1995, 107, 2459-2461; Angew. Chem. Int. Ed. Engl. 1995, 34, 2254-2256.
29. a) S. S. Wong, M. N. Paddon-Row. J. Chem. Soc. Chem. Commun. 1991, 327- 330;
30. b) S. S. Wong, M. N. Paddon-Row, Aust. J. Chem. 1991, 44, 765-770;
31. c) Y.-D. Wu, J. A. Tucker, K. N. Houk, J. Am. Chem. Soc. 1991, 113, 5018- 5027;
32. d) M. N. Paddon-Row, Y.-D. Wu, K. N. Houk, ibid. 1992, 114,10638- 10639;
33. e) Y-D. Wu, Y Li, J. Na. K. N. Houk, J. Org. Chem. 1993, 58, 4625- 4628;
34. f) W. Adcock, J. Cotton, N. A. Trout, ibid. 1994, 59, 1867-1876;
35. g) D. K. Jones, D. C. Liotta, W.-B. Choi, R. P. Volante, P. J. Reider, I. Shinkai, H. R. O. Churchill, J. E. Lynch, ibid. 1994, 59, 3749-3751;
36. h) R. K. Boeckmun, B. T. Connell, J. Am. Chem. Soc. 1995. 117,12368-12369;
37. i) A. Ohno, A. Tsutsumi, N. Yamazaki, M. Okamura, Y Mikata, M. Fujii, Bull. Cltem. Soc. Jpn. 1996, 69, 1679-1685.
38. P. Wipf, Y. Kim, J. Am. Client. Soc. 1994, 116, 11678-11688.
39. a) G. Schlingman,. R. R. West, L. Milne, C. J. Pearce, G. T. Carter, Tetrahedron Lett. 1993, 34, 7225-7228;
40. b) M. Chu, I. Truumees, M. G. Patel, V. P. Gullo, M. S. Puar, A. T. McPhail, J. Org. Chem. 1994, 59, 1222-1223;
41. c) R. Thiergardt, G. Rihs, P. Hug, H. H. Peter, Tetrahedron 1995, 51, 733-742.
42. G. Schlingmann, S. Matile, N. Berova, K. Nakanishi, G. T. Carter, Tetrahedron 1996, 52, 433-446.
43. We thank Dr. Steven Geib (University of Pittsburgh, USA) for performing single-crystal X-ray structure analyses of 11 and 26. Crystallographic data will be reported elsewhere; P. Wipf, J.-K. Jung, S. J. Geib, Acta Cryst. C, submitted.
44. J. Gao, X. Xia, Science 1992, 258, 631-635, and references therein.
45. 4 , saponification, resolution according to Seebach's protocol, monomethylation with MeLi, syn-selective reduction with diisobutylaluminum hydride, and C4-selective Mitunobu inversion. M. Acs. C. von dem Bussche, D. Seebach, Chimia 1990, 44, 90-92.
46. P. Wipf, Y. Kim, P. C. Fritch, J. Org. Chem. 1993, 55, 7195-7203, and references therein.