Palladium-catalyzed aryl-amidation. Synthesis of non-racemic N-aryl lactams

Tetrahedron

Volumn 60, Issue 2, 2004, Pages 359-365

  Browning, R Greg ^a   Badarinarayana, Vivek ^a   Mahmud, Hossen ^a   Lovely, Carl J ^a  

^a UNIVERSITY OF TEXAS AT ARLINGTON   (United States)

Author keywords

Catalysis; Cross coupling; Pyrrolidinone

Indexed keywords

1 (4 BENZOYLPHENYL) 5 TERT BUTYLDIMETHYLSILYLOXYMETHYL 2 PYRROLIDINONE; 1 (4 BROMOPHENYL) 5 TERT BUTYLDIMETHYLSILYLOXYMETHYL 2 PYRROLIDINONE; 2 (2 TERT BUTYLDIMETHYLSILYLOXYMETHYL 5 OXO 1 PYRROLIDINYL)BENZONITRILE; 4 (2 CARBOMETHOXYMETHYL 5 OXO 1 PYRROLIDINYL)BENZONITRILE; 4 (2 CYANOMETHYL 5 OXO 1 PYRROLIDINYL)BENZONITRILE; 4 (2 TERT BUTYLDIMETHYLSILYLOXYMETHYL 5 OXO 1 PYRROLIDINYL)BENZONITRILE; 4 [2 [2 (TERT BUTYLDIMETHYLSILYLOXY)ETHYL] 5 OXO 1 PYRROLIDINYL]BENZONITRILE; 5 TERT BUTYLDIMETHYLSILYLOXYMETHYL 1 (2 NITROPHENYL) 2 PYRROLIDINONE; 5 TERT BUTYLDIMETHYLSILYLOXYMETHYL 1 (3 METHOXYPHENYL) 2 PYRROLIDINONE; 5 TERT BUTYLDIMETHYLSILYLOXYMETHYL 1 (4 NITROPHENYL) 2 PYRROLIDINONE; 5 TERT BUTYLDIMETHYLSILYLOXYMETHYL 1 PHENYL 2 PYRROLIDINONE; 5 TERT BUTYLDIMETHYLSILYLOXYMETHYL 1 [(4 TRIFLUOROMETHYL)PHENYL] 2 PYRROLIDINONE; 5 [2 (TERT BUTYLDIMETHYLSILYLOXY)ETHYL] 1 (4 NITROPHENYL) 2 PYRROLIDINONE; BROMINE DERIVATIVE; ETHYL 4 (2 TERT BUTYLDIMETHYLSILYLOXYMETHYL 5 OXO 1 PYRROLIDINYL)BENZOATE; LACTAM DERIVATIVE; PALLADIUM; PYRROLIDINE DERIVATIVE; UNCLASSIFIED DRUG;

AMIDATION; ARTICLE; CATALYSIS; CHIRALITY; CROSS COUPLING REACTION; DRUG STRUCTURE; DRUG SYNTHESIS; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; STRUCTURE ANALYSIS;

EID: 0346887155     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2003.11.008     Document Type: Article

References (53)

1. Witherup K.M., Ransom R.M., Graham A.C., Bernard A.M., Salvatore M.J., Lumma W.C., Anderson P.S., Pitzenberger S.M., Varga S.L. J. Am. Chem. Soc. 117:1995;6682.
2. Gurjar M.K., Pal S., Rao A.V.R. Heterocycles. 45:1997;231.
3. (a) Ho T.C.T., Jones K. Tetrahedron. 53:1997;8287.
4. (b) Escalero C., Jones K. Tetrahedron Lett. 41:2000;8951.
5. Kim S.S., Cheon H.G., Kang S.K., Yum E.K., Choi J.K. Heterocycles. 48:1998;221.
6. (a) Hadden M., Stevenson P.J. Tetrahedron Lett. 40:1999;1215.
7. (b) Hadden M., Nieuwenhuyzen M., Osborne D., Stevenson P.J., Thompson N. Tetrahedron Lett. 42:2001;6417.
8. (c) Hadden M., Nieuwenhuyzen M., Potts D., Stevenson P.J., Thompson N. Tetrahedron. 57:2001;5615.
9. (a) Lovely C.J., Mahmud H. Tetrahedron Lett. 40:1999;2079.
10. (b) Mahmud H., Lovely C.J., Dias H.V.R. Tetrahedron. 57:2001;4095.
11. (c) He Y., Mahmud H., Wayland B.R., Dias H.V.R., Lovely C.J. Tetrahedron Lett. 43:2002;1171.
12. (a) Snider B.B., Ahn Y., Foxman B.M. Tetrahedron Lett. 40:1999;3339.
13. (b) Snider B.B., O'Hare S.M. Tetrahedron Lett. 42:2001;2455.
14. (c) Snider B.B., Ahn Y., O'Hare S.M. Org. Lett. 3:2001;4217.
15. (a) Batey R.A., Simoncic P.D., Lin D., Smyj R.P., Lough A.J. Chem. Commun. 1999;651.
16. (b) Batey R.A., Powell D.A. Chem. Commun. 2001;2362.
17. (c) Powell D.A., Batey R.A. Org. Lett. 4:2002;2913.
18. Frank K.E., Aubé. J. Org. Chem. 65:2000;655.
19. Nieman J.A., Ennis M.D. Org. Lett. 2:2000;1395.
20. (a) Ma D., Xia C., Jiang J., Zhang J. Org. Lett. 3:2001;2189.
21. (b) Xia C., Heng L., Ma D. Tetrahedron Lett. 43:2002;9405.
22. (c) Ma D., Xia C., Jiang J., Zhang J., Tang W. J. Org. Chem. 68:2003;442.
23. (a) Nyerges M., Fejes I., Toke L. Tetrahedron Lett. 41:2000;7951.
24. (b) Nyerges M., Fejes I., Toke L. Synthesis. 2002;1823.
25. Malassene R., Sanchez-Bajo L., Toupet L., Hurvois J.-P., Moinet C. Synlett. 9:2002;1500.
26. (a) Hartwig J.F. Synlett. 1997;330.
27. (b) Hartwig J.F. Angew. Chem., Int. Ed. Engl. 37:1998;2046.
28. (c) Yin J., Buchwald S.L. Org. Lett. 2:2000;1101.
29. (d) Yang B.H., Buchwald S.L. J. Organomet. Chem. 576:1999;125.
30. Non-racemic N-aryl hydroxymethylpyrrolidinones can be prepared from protected hydroxymethylbutyrolactones (three steps from glutamic acid) and anilines by acylation, hydroxyl activation and intramolecular substitution Fujita M., Kitagawa O., Yamada Y., Izawa H., Hasegawa H., Taguchi T. J. Org. Chem. 65:2000;1108.
31. An aromatic nucleophilic ipso substitution approach was reported in which the N-aryl bond was formed by heating an HMPA solution of the pyroglutamic acid dianion with an activated fluorobenzene at 160 °C for 23 h, giving the product in 40% yield Atigadda V.R., Brouliette W.J., Duarte F., Ali S.M., Babu Y.S., Bantia S., Chand P., Chu N., Montgomery J.A., Walsh D.A., Sudbeck E.A., Finley J., Luo M., Air G.M., Laver G.W. J. Med. Chem. 42:1999;2332.
32. Chan D.M.T. Tetrahedron Lett. 37:1996;9013.
33. Chan D.M.T., Monaco K.L., Wang R.-P., Winters M.P. Tetrahedron Lett. 39:1998;2933.
34. Klapars A., Huang X., Buchwald S.L. J. Am. Chem. Soc. 124:2002;7421.
35. Cacchi S., Fabrizi G., Goggiamani A., Zappia G. Org. Lett. 3:2001;2539.
36. Madar D.J., Kopecka H., Pireh D., Pease J., Pliushchev M., Sciotti R.J., Wiedeman P.E., Djuric S.W. Tetrahedron Lett. 42:2001;3681.
37. Hartwig J.F., Kawatsura M., Hauck S.I., Shaughnessy K.H., Alcazar-Roman L.M. J. Org. Chem. 64:1999;5575.
38. Wakaki S., Marumo H., Tomoika K., Shimizu G., Kato E., Kamada H., Kudo S., Fujimoto Y. Antibiot. Chemother. 8:1958;228.
39. Tokuyama T., Uenoyama K., Brown G., Daly J.W., Witkop B. Helv. Chim. Acta. 57:1974;2597.
40. A prelimnary report describing this work has appeared Browning R.G., Mahmud H., Badarinarayana V., Lovely C.J. Tetrahedron Lett. 42:2001;7155.
41. Shakespeare W.C. Tetrahedron Lett. 40:1999;2035.
42. Nagawa Y., Matsumoto K., Tomioka K. Tetrahedron. 56:2000;2857.
43. (a) Yang B.H., Buchwald S.L. Org. Lett. 1:1999;35.
44. (b) Yin J., Buchwald S.L. Org. Lett. 2:2000;1101.
45. Madder A., Munster I., Rolle U., de Clercq P.J. Bull. Soc. Chem. Belg. 106:1997;613.
46. Ackermann J., Mathes M., Tamm C. Helv. Chim. Acta. 73:1990;122.
47. (±)-11 was prepared in 22% overall yield (4 steps from (±)-glutamic acid) according to the procedure of Tamm and co-workers for the optically active compound, see Ref. 28.
48. (a) Pirkle W.H., Sikkenga D.L. J. Org. Chem. 42:1977;1370.
49. (b) Pirkle W.H., Adams P.E. J. Org. Chem. 43:1978;378.
50. (c) Pirkle W.H., Hauske J.R. J. Org. Chem. 42:1977;2436.
51. (d) Pirkle W.H., Hoekstra M.S. J. Am. Chem. Soc. 98:1976;1832.
52. The enantiomeric purities of the higher homologs ( 16 , 17 , 18a,b ) were not established experimentally since there was no evidence of racemization in any of the lower homologs.
53. For general details see Ref. 6b.