A potentially general intramolecular biaryl coupling approach to optically pure 2,2'-BINOL analogs

Tetrahedron Letters

Volumn 38, Issue 5, 1997, Pages 753-756

  Lipshutz, Brace H ^a   James, Brian ^a   Vance, Shelly ^a   Cairico, Isaac ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1,1' BINAPHTHYL DERIVATIVE; MACROCYCLIC COMPOUND;

ARTICLE; CATALYSIS; CHIRALITY; DRUG SYNTHESIS; METHODOLOGY;

EID: 0031016066     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(96)02453-7     Document Type: Article

References (43)

1. Rosinio, C; Franzini, L.; Raffaelli, A. Salvadori, P. Synthesis, 1992, 503.
2. (a) Cram, D. J.; Cram, J. M. Acc. Chem. Res. 1978, 11, 8.
3. (b) Jacques, J.; Fouquay, C. Tetrahedron Lett. 1971, 4617.
4. (c) Noyori, R.; Tomino, I.; Tanimoto, Y. J. Am. Chem Soc. 1979, 101, 3129.
5. (a) Jacques, J.; Fouquay, C. Org. Synth. 1988, 67, 1.
6. (b) Truesdale, L. Org. Synth. 1988, 67, 13.
7. Mazalerat, J. -P.; Wakselman, M. J. Org. Chem. 1996, 61, 2695.
8. (a) Fujimoto, Y.; Iwadate, H.; Ikekawa, N. J. Chem. Soc., Chem. Commun. 1985, 1333.
9. (b) Kazlaukas, R. J. J. Am. Chem. Soc. 1989, 111, 4953.
10. For examples, see Ishihara, K.; Yamamoto, H. J. Am. Chem. Soc. 1994, 116, 1561; Bao, J.; Wulff, W.D. ibid., 1993, 115, 3814.
11. For examples, see Ishihara, K.; Yamamoto, H. J. Am. Chem. Soc. 1994, 116, 1561; Bao, J.; Wulff, W.D. ibid., 1993, 115, 3814.
12. See, e.g., Maruoka, K.; Saito, S.; Yamamoto, H. J. Am. Chem. Soc. 1995, 117, 1165.
13. Barany, G.; Merrifleld, R.B. in The Peptides, Gross, E., Metenhofer, J., Eds., Academic Press, N.Y., 1979, Vol 2, p1.
14. Han, H.; Janda, K.D. J. Am. Chem. Soc. 1996, 118, 7632.
15. Kolb, H. C.; VanNieuwenhze, M. S.; Sharpless, K. B. Chem. Rev. 1994, 94, 2483.
16. (a) Hughes, D. L Org. React. 1992, 42, 335;
17. (b) Mitsunobu, O. Synthesis 1981, 1.
18. 3,N and DMAP.
19. (a) Dale, J. A.; Dull, D. L; Mosher, H. S. J. Org. Chem. 1969, 34, 2543.
20. (b) Dale, J. A.; Mosher, H. S. J. Am.. Chem.. Soc 1973, 95, 512
21. Noji, M.; Nakajima, M.; Koga, K. Tetrahedron Lett. 1994, 35, 7983.
22. We suggest that cyclo-BINOLs be named according to tether length. Compound 7 is an 8-cyclo-BINOL, which is modified by the oxygens at the 1″ and 8″ positions; hence l″,8″-di-O-8-cyclo-BINOL.
23. Cu(II): (a) Feringa, B.; Wynberg, H. Tetrahedron Lett. 1977, 4447.
24. (b) Sakamoto, T.; Yonehara, H; Pac, C. J. Org. Chem. 1994, 59, 6859.
25. (c) Brusee, J.; Groenedijk, J. L. G.; te Koppele, J. M.; Jansen, A. C. A. Tetrahedron 1985, 41, 3313.
26. (d) Kushioka, K J. Org. Chem. 1983, 48, 4948.
27. (e) Noji, M.; Nakajima, M.; Koga, K. Tetrahedron Lett. 1994, 35, 7983.
28. Fe(III): (f) Pummerer, R.; Rieche, A. Chem. Ber. 1926, 59.
29. (g) Toda, F.; Tanaka, K.; Iwata, S. J. Org. Chem. 1989, 54, 3007.
30. Mn(III): (h) Dewar, M. J. S.; Nakaya, T. J. Am. Chem. Soc. 1968, 90, 7134.
31. (a) Keck, G. E.; Tarbet, K. H.; Geraci, L. S. J. Am. Chem. Soc. 1993, 115, 8467; see also Costa, A.L.; Piazza, M.G.; Tagliavini, E.; Trombini, C.; Umani-Ronchi, A. ibid., 1993, 115, 7001.
32. (a) Keck, G. E.; Tarbet, K. H.; Geraci, L. S. J. Am. Chem. Soc. 1993, 115, 8467; see also Costa, A.L.; Piazza, M.G.; Tagliavini, E.; Trombini, C.; Umani-Ronchi, A. ibid., 1993, 115, 7001.
33. (b) Keck. G. E.; Geraci, L. S. Tetrahedron Lett. 1993, 34, 7827.
34. (c) Brown, H.C.; Jadhav, P.K. J. Am. Chem. Soc. 1983, 105, 2092;
35. Faller, J.W.; Sams, D.W.I.; Liu, X. ibid., 1996, 118, 1217;
36. (e) Weigand, S.; Bruckner, R. Angew. Chem. Int. Ed. Engl. 1996, 35, 1077;
37. (f) Yu, C-M.; Choi, H-S.; Jung, W-H.; Lee, S-S. Tetrahedron Lett. 1996, 37, 7095.
38. The catalyst could be routinely recovered from each reaction mixture in 70-75% yields.
39. Molecular Mechanics calculations were performed using the MM3 force field as applied by the Chem3D modeling program version 3.1. Copyright 1986-1995, CambridgeSoft Corporation.
40. Guillaneux, D.; Zhao, S.-H.; Samuel O.; Rainford, D.; Kagan, H.B. J. Am. Chem. Soc. 1994, 116, 9430.
41. Keck, G.E.; Krishnamurthy, D.; Grier, M.C J. Org. Chem. 1993, 58, 6543.
42. For related work with biphenyls, see Harada, T.; Ueda, S.; Yoshida, T.; Inoue, A.; Takeuchi, M.; Ogawa, N.; Oku, A.; Shiro, M. J. Org. Chem. 1994, 59, 7575.
43. Cai, D.; Payack, J. F.; Bender, D. R.; Hughes, D. L; Verhoeven, T. R; Reider, P. J. J. Org. Chem. 1994, 59, 7180.