Synthesis of arylglycines via the Dötz benzannulation reaction

Tetrahedron Letters

Volumn 46, Issue 52, 2005, Pages 9039-9042

  Pulley, Shon R ^a,c   Czakó, Barbara ^b   Brown, Gregory D ^a  

^a UNIVERSITY OF MISSOURI   (United States)

^b UNIVERSITY OF PENNSYLVANIA   (United States)

^c ELI LILLY AND COMPANY   (United States)

Author keywords

Arylglycine; Dotz benzannulation

Indexed keywords

ALKYNE DERIVATIVE; CHROMIUM DERIVATIVE; GLYCINE DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE;

ARTICLE; CHEMICAL REACTION; DECOMPOSITION; DOTZ BENZANNULATION REACTION; DRUG SYNTHESIS; OXIDATION;

EID: 28244437729     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.10.105     Document Type: Article

References (41)

1. R.W. Williams, and J.A. Hendrix Chem. Rev. 92 1992 889
2. J. Watkins, and G. Collingridge Trends Pharm. Sci. 15 1994 333
3. J.S. Bedingfield, M.C. Kemp, D.E. Jane, H.W. Tse, P.J. Roberts, and J. Watkins Br. J. Pharmacol. 116 1995 3323
4. M.H. McCormic, W.M. Stark, G.F. Pittenger, R.C. Pittenger, and G.M. McGuire Antibiot. Annu. 9 1955-1956 606
5. C.M. Harris, J.J. Kibby, J.R. Fehlner, H.B. Raabe, T.A. Barber, and T.M. Harrus J. Am. Chem Soc. 101 1979 437
6. C. Coronelly, M.R. Bardone, A. DePaoli, P. Ferrari, G. Tuan, and G.G. Gallo J. Antibiot. 37 1984 621
7. C.A. Townsand, and A.M. Brown J. Am. Chem. Soc. 105 1983 913
8. T. Kamiya, M. Hashimoto, O. Nakaguchi, and T. Oku Tetrahedron 35 1979 323
9. E.M. Meijer, W.H.J. Boesten, H.E. Shoemaker, and J.A.M. Balken Studies in Organic Chemistry 1985 Elsevier Amsterdam
10. R.W. Williams, and J.A. Hendrix Chem. Rev. 92 1992 889
11. K. Weinges, G. Brune, and H. Droste Liebigs Ann. Chem. 2 1980 212
12. K. Weinges, K.P. Koltz, and H. Droste Chem. Ber. 113 1980 722
13. K. Weinges, H. Brachmann, P. Stahnecker, H. Rodewald, M. Nixdorf, and H. Irngartinger Liebigs Ann. Chem. 3 1985 566
14. U. Schollkopf, S. Guttner, R. Anderskewitz, E. Egert, and M. Dyrbusch Angew. Chem., Int. Ed. 26 1987 683
15. W. Harwig, and U. Schollkopf Liebigs Ann. Chem. 11 1982 1952
16. W. Oppoltzer, and O. Tamura Tetrahedron Lett. 31 1990 991
17. D.A. Evans, and S.G. Nelson J. Am. Chem. Soc. 119 1997 6452
18. D.A. Evans, J.A. Ellman, and R.L. Dorow Tetrahedron Lett. 28 1987 1123
19. D.A. Evans, T.C. Britton, J.A. Ellman, and R.L. Dorow J. Am. Chem. Soc. 112 1990 4011
20. K.L. Reddy, and K.B. Sharpless J. Am. Chem. Soc. 120 1998 1207
21. K.H. Dötz Angew. Chem., Int. Ed. 14 1975 644
22. W.D. Wulff, and S.R. Gilbertson J. Am. Chem. Soc. 107 1985 503
23. R. Aumann, and E.O. Fischer Chem. Ber. 101 1968 945
24. R. Aumann, and H. Heinen Chem. Ber. 120 1987 5379
25. T.H. Chan, W. Mychajlowski, B.S. Ong, and D.N. Harpp J. Org. Chem. 43 1978 1526
26. W.D. Wulff, and B. Bax Tetrahedron 49 1993 5331
27. J.A. Connor, and E.M. Jones J. Chem. Soc. A 21 1971 3368
28. P. Garner, and J.M. Park Synthesis 70 1991 18
29. S. Ohira Synth. Commun. 19 1989 561
30. J.P.A. Harrity, J.W. Kerr, and D. Middlemiss Tetrahedron 49 1993 5565
31. 2 oxidation of 7b, and the N-Boc-protected derivative of the same compound was compared. Indeed, the oxidation of the N-Cbz-protected arylglycinol proceeded with higher yield (70% vs 43%).
32. M. Zhao, J. Li, Z. Song, R. Desmond, D.M. Tschaen, E.J.J. Grabowsky, and P.J. Reider Tetrahedron Lett. 39 1998 5323
33. P.H.J. Carlsen, T. Katsuki, and V.S. Martin J. Org. Chem. 46 1981 3936
34. W.P. Griffith, S.V. Ley, G.P. Whitcombe, and A.D. White J. Chem. Soc., Chem. Commun. 1987 1625
35. K.L. Reddy, and K.B. Sharpless J. Am. Chem. Soc. 120 1998 1207
36. M.R. Leanna, T.J. Sowin, and H.E. Morton Tetrahedron Lett. 1992 5029
37. A.J. Mancuso, S.L. Huang, and D. Swern J. Org. Chem. 43 1978 2480
38. K. Omura, and D. Swern Tetrahedron 34 1978 1651
39. D.B. Dess, and J.C. Martin J. Org. Chem. 48 1983 4155
40. B.S. Bal, W.E. Childers, and H.W. Pinnic Tetrahedron 37 1981 2091
41. For full characterization, the resulting acids were converted to the corresponding methyl esters by diazomethane.