Towards diversity-oriented, stereoselective syntheses of biaryl- or bis(aryl)metal-containing medium rings [11]

Journal of the American Chemical Society

Volumn 122, Issue 23, 2000, Pages 5656-5657

  Spring, David R ^a   Krishnan, Shyam ^a   Schreiber, Stuart L ^a  

^a HARVARD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CYANIDE; LITHIUM DERIVATIVE; METAL DERIVATIVE; METHYL BROMIDE; NITROBENZENE DERIVATIVE; TERT BUTYLLITHIUM; UNCLASSIFIED DRUG;

AMINATION; CHEMICAL STRUCTURE; CHIRALITY; CYCLIZATION; ISOMERISM; KINETICS; LETTER; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION; STRUCTURE ANALYSIS; SYNTHESIS; THERMAL EXPOSURE; THERMODYNAMICS;

EID: 0034647234     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0010507     Document Type: Letter

References (38)

1. Schreiber, S. L. Bioorg. Med. Chem. 1998, 6, 1127-1152.
2. (b) Mitchison, T. J. Chem. Biol. 1994, 1, 3-6.
3. (c) http.//www-schreiber.chem.harvard.edu.
4. (d) http://iccb.med.harvard.edu.
5. (a) Nicolaou, K. C.; Boddy, C. N. C.; Brase, S.; Winssinger, N. Angew. Chem., Int. Ed. 1999, 38, 2097-2152.
6. (b) Quideau, S.; Feldman, K. S. Chem. Rev. 1996, 96, 475-503.
7. For example, gossypol occurs naturally as both atropisomers; the M isomer is a male contraceptive, whereas the P isomer lacks this activity and is toxic to cells. Huang, L.; Si, Y. K.; Snatzke, G.; Zheng, D. K.; Zhou, J. Collect. Czech. Chem. Commun. 1988, 53, 2664-2666.
8. (a) Schreiber, S. L. Science 2000, 287, 1964-1969.
9. (b) Lee, D.; Sello, J. K., Schreiber, S. L. Org. Lett. 2000, 2, 709-712.
10. (a) Furka, A.; Sebestyén, F.; Asgedom, M.; Dibó, G. Int. J. Pept. Protein Res. 1991, 37, 487-493.
11. (b) Lam, K. S.; Salmon, S. E.; Hersh, E. M.; Hruby, V. J.; Kazmierski, W. M.; Knapp, R. J. Nature 1991, 354, 82-84.
12. (c) Houghten, R. A.; Pinilla, C.; Blondelle, S. E.; Appel, J. R.; Dooley, C. T.; Cuervo, J. H. Nature 1991, 354, 84-86.
13. Lee, D.; Sello, J. K. Schreiber, S. L. J. Am. Chem. Soc. 1999, 121, 10648-10649.
14. For recent reviews of biaryl synthesis: (a) Bringmann, G.; Breuning, M.; Tasler, S. Synthesis 1999, 525-558.
15. (b) Stanforth, S. P. Tetrahedron 1998, 54, 263-303.
16. (a) Ullmann, F.; Bielecki, J. Chem. Ber. 1901, 34, 2174-2185.
17. (b) Konduirov, N. V.; Fomin, D. A. J. Russ. Phys. Chem. Soc. 1915, 47, 190-198 (Chem. Abstr. 1915, 9, 1473).
18. (b) Konduirov, N. V.; Fomin, D. A. J. Russ. Phys. Chem. Soc. 1915, 47, 190- 198 (Chem. Abstr. 1915, 9, 1473).
19. (a) Whitesides, G. M.; Stedronsky, E. R.; Casey, C. P.; San Filippo, J., Jr. J. Am. Chem. Soc. 1970, 92, 1426-1427 and references therein.
20. (b) Kauffmann, T. Angew. Chem., Int. Ed. Engl. 1974, 13, 291-305.
21. (c) van Koten, G.; Jastrzebski, J. T. B. H.; Noltes, J. G. J. Org. Chem. 1977, 42, 2047-2053.
22. (d) Ziegler, F. E.; Chliwner, I.; Fowler, K. W.; Kanfer, S. J.; Kuo, S. J.; Sinha, N. D. J. Am. Chem. Soc. 1980, 102, 790-798.
23. (e) Bertz, S. H.; Gibson, C. P. J. Am. Chem. Soc. 1986. 108, 8286-8288.
24. (a) Lipshutz, B. H.; Siegmann, K.; Garcia, E. J. Am. Chem. Soc. 1991, 113, 8161-8162.
25. (b) Lipshutz, B. H.; Siegmann, K.; Garcia, E. Tetrahedron 1992, 48, 2579-2588.
26. (c) Lipshutz, B. H.; Siegmann, K.; Garcia, E.; Kayser, F. J. Am. Chem. Soc. 1993, 115, 9276-9282.
27. (d) Lipshutz, B. H.; Kayser, F.; Siegmann, K. Tetrahedron Lett. 1993, 34, 6693-6696.
28. (e) Lipshutz, B. H.; Kayser, F.; Liu, Z.-P. Angew. Chem., Int. Ed. Engl. 1994, 33, 1842-1844.
29. (f) Lipshutz, B. H.; Kayser, F.; Maullin, N. Tetrahedron Lett. 1994, 35, 815-818.
30. (g) Lipshutz, B. H.; Liu, Z.-P.; Kayser, F. Tetrahedron Lett. 1994, 35, 5567-5570.
31. 2 (5:1).
32. Typical concentrations of 1 were between 0.05 and 0.15 M, and was limited only by the solubility of the bis-aryllilhium.
33. Also, 3,3′-dinitroazoxybenzene and excess 1,3-DNB were observed in the crude reaction mixture.
34. The conformational preference for 3e-g is to have the biaryl axis distorted from planarity in the same conformation as (M)-3a.
35. Sinnott, M. L. Adv. Phys. Org. Chem. 1988, 24, 113-204.
36. Tallarico, J. A.; Depew, K. M. Pelish, H. E.; Athanasopoulos, J.; Lindsley, C. W.; Westwood, N. J.; King, R. W.; Schreiber, S. L.; Shair, M. D.; Foley, M. A., unpublished results.
37. (a) Mayer, T. U.; Kapoor, T. M.; Haggarty, S. J.; King, R. W.; Schreiber, S. L.; Mitchison, T. J. Science 1999, 286, 971-974.
38. (b) Stockwell, B. R.; Haggarty, S. J.; Schreiber, S. L. Chem. Biol. 1999, 6, 71-83.