Stereoselective synthesis of imidazolidin-2-ones via Pd-catalyzed alkene carboamination. Scope and limitations

Tetrahedron

Volumn 64, Issue 29, 2008, Pages 6838-6852

  Fritz, Jonathan A ^a   Wolfe, John P ^a  

^a UNIVERSITY OF MICHIGAN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

3 ETHYL 1 METHYL 4 (NAPHTHALEN 1 YLMETHYL)IMIDAZOLIDIN 2 ONE; 3 ETHYL 1 METHYL 4 (NAPHTHALEN 2 YLMETHYL) IMIDAZOLIDIN 2 ONE; 3 ETHYL 4 (4 METHYLBENZYL) 1 PHENYLIMIDAZOLIDIN 2 ONE; 3 ETHYL 4 (NAPHTHALEN 2 YLMETHYL) 1 PHENYLIMIDAZOLIDIN 2 ONE; 3 ETHYL 4 METHYL 1 PHENYL 1,3 DIHYDROIMIDAZOL 2 ONE; 4 (4 TERT BUTYLBENZYL) 3 ETHYL 1 METHYLIMIDAZOLIDIN 2 ONE; IMIDAZOLIDIN 2 ONE; IMIDAZOLIDINE DERIVATIVE; ISOCYANATE;

AMINATION; ARTICLE; CHEMICAL REACTION; CHROMATOGRAPHY; OLEFINATION; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; SYNTHESIS;

HUMAN ECHOVIRUS 1;

EID: 44949263787     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2008.04.015     Document Type: Article

References (100)

1. De Lucca G.V., and Lam P.Y.S. Drugs Future 23 (1998) 987-994
2. Salituro F.G., Baker C.T., Court J.J., Deininger D.D., Kim E.E., Li B., Novak P.M., Rao B.G., Pazhanisamy S., Porter M.D., Schairer W.C., and Tung R.D. Bioorg. Med. Chem. Lett. 8 (1998) 3637-3642
3. Spaltenstein A., Almond M.R., Bock W.J., Cleary D.G., Furfine E.S., Hazen R.J., Kazmierski W.M., Salituro F.G., Tung R.D., and Wright L.L. Bioorg. Med. Chem. Lett. 10 (2000) 1159-1162
4. De Clerq E. Biochim. Biophys. Acta 1587 (2002) 258-275
5. Kazmierski W.M., Furfine E., Gray-Nunez Y., Spaltenstein A., and Wright L. Bioorg. Med. Chem. Lett. 14 (2004) 5685-5687
6. Heidempergher F., Pillan A., Pinciroli V., Vaghi F., Arrigoni C., Bolis G., Caccia C., Dho L., McArthur R., and Varasi M. J. Med. Chem. 40 (1997) 3369-3380
7. Reichard G.A., Stengone C., Paliwal S., Mergelsberg I., Majmundar S., Wang C., Tiberi R., McPhail A.T., Piwinkski J.J., and Shih N.-Y. Org. Lett. 5 (2003) 4249-4251
8. Shue H.-J., Chen X., Shih N.-Y., Blythin D.J., Paliwal S., Lin L., Gu D., Schwerdt J.H., Shah S., Reichard G.A., Piwinski J.J., Duffy R.A., Lachowicz J.E., Coffin V.L., Liu F., Nomeir A.A., Morgan C.A., and Varty G.B. Bioorg. Med. Chem. Lett. 15 (2005) 3896-3899
9. Shue H.-J., Chen X., Schwerdt J.H., Paliwal S., Blythin D.J., Lin L., Gu D., Wang C., Reichard G.A., Wang H., Piwinski J.J., Duffy R.A., Lachowicz J.E., Coffin V.L., Nomeir A.A., Morgan C.A., Varty G.B., and Shih N.-Y. Bioorg. Med. Chem. Lett. 16 (2006) 1065-1069
10. Kim J.-M., Wilson T.E., Norman T.C., and Schultz P.G. Tetrahedron Lett. 37 (1996) 5309-5312
11. Cardillo G., D'Amico A., Orena M., and Sandri S. J. Org. Chem. 53 (1988) 2354-2356
12. Davies S.G., and Mortlock A.A. Tetrahedron Lett. 32 (1991) 4791-4794
13. Sankhavasi W., Yamamoto M., Kohmoto S., and Yamada K. Bull. Chem. Soc. Jpn. 64 (1991) 1425-1427
14. Taguchi T., Shibuya A., Sasaki H., Endo J.-i., Morikawa T., and Shiro M. Tetrahedron: Asymmetry 5 (1994) 1423-1426
15. Davies S.G., Evans G.B., and Mortlock A.A. Tetrahedron: Asymmetry 5 (1994) 585-606
16. Kubota H., Kubo A., Takahashi M., Shimizu R., Da-te T., Okamura K., and Nunami K.-i. J. Org. Chem. 60 (1995) 6776-6784
17. Palomo C., Oiarbide M., Gonzalez A., Garcia J.M., and Berree F. Tetrahedron Lett. 37 (1996) 4565-4568
18. Guillena G., and Najera C. Tetrahedron: Asymmetry 9 (1998) 1125-1129
19. Wulff W.D. Organometallics 17 (1998) 3116-3134
20. Parisi M., Solo A., Wulff W.D., Guzei I.A., and Rheingold A.L. Organometallics 17 (1998) 3696-3700
21. Kise N., Ueda T., Kumada K., Terao Y., and Ueda N. J. Org. Chem. 65 (2000) 464-468
22. Guillena G., and Nájera C. J. Org. Chem. 65 (2000) 7310-7322
23. Cardillo G., Orena M., Penna M., Sandri S., and Tomasini C. Tetrahedron 47 (1991) 2263-2272
24. Trost B.M., and Fandrick D.R. J. Am. Chem. Soc. 125 (2003) 11836-11837
25. Sartori G., and Maggi R. In: Ley S.V., and Knight J.G. (Eds). Science of Synthesis (Houben-Weyl Methods of Molecular Transformations) Vol. 18 (2005), Thieme, Stuttgart 665-758
26. Qian F., McCusker J.E., Zhang Y., Main A.D., Chlebowski M., Kokka M., and McElwee-White L. J. Org. Chem. 67 (2002) 4086-4092
27. Gabriele B., Salerno G., Mancuso R., and Costa M. J. Org. Chem. 69 (2004) 4741-4750
28. Lucet D., Gall T.L., and Mioskowski C. Angew. Chem., Int. Ed. 37 (1998) 2580-2627
29. For synthesis of imidazolidin-2-ones via ring expansion reactions of aziridines, see Ref. 7. See also:
30. Zhou H.-B., and Alper H. J. Org. Chem. 68 (2003) 3439-3445
31. Kim M.S., Kim Y.-W., Hahm H.S., Jang J.W., Lee W.K., and Ha H.-J. Chem. Commun. (2005) 3062-3064
32. For synthesis of imidazolidin-2-ones via iodocyclization of N-allylureas, see:
33. Hunt P.A., May C., and Moody C.J. Tetrahedron Lett. 29 (1988) 3001-3002
34. Balko T.W., Brinkmeyer R.S., and Terando N.H. Tetrahedron Lett. 30 (1989) 2045-2048
35. Fujita M., Kitagawa O., Suzuki T., and Taguchi T. J. Org. Chem. 62 (1997) 7330-7335
36. For synthesis of imidazolidin-2-ones via alkene diamination, see:
37. Bar G.L.J., Lloyd-Jones G.C., and Booker-Milburn K.I. J. Am. Chem. Soc. 127 (2005) 7308-7309
38. Zabawa T.P., Kasi D., and Chemler S.R. J. Am. Chem. Soc. 127 (2005) 11250-11251
39. Streuff J., Hövelmann C.H., Nieger M., and Muñiz K. J. Am. Chem. Soc. 127 (2005) 14586-14587
40. Du H., Zhao B., and Shi Y. J. Am. Chem. Soc. 129 (2007) 762-763
41. Yuan W., Du H., Zhao B., and Shi Y. Org. Lett. 9 (2007) 2589-2591
42. For synthesis of imidazolidin-2-ones via intramolecular alkane C-H bond functionalization, see:. Kim M., Mulcahy J.V., Espino C.G., and Du Bois J. Org. Lett. 8 (2006) 1073-1076
43. For synthesis of imidazolidin-2-ones via intramolecular N-arylation of N-(2-haloraryl)ureas, see:
44. McLaughlin M., Palucki M., and Davies I.W. Org. Lett. 8 (2006) 3311-3314
45. Benedí C., Bravo F., Uriz P., Fernandez E., Claver C., and Castillon S. Tetrahedron Lett. 44 (2003) 6073-6077
46. For synthesis of imidazolidin-2-ones via intramolecular allylic alkylation, see:. Overman L.E., and Remarchuk T.P. J. Am. Chem. Soc. 124 (2002) 12-13
47. Tamaru Y., Hojo M., Higashimura H., and Yoshida Z.-i. J. Am. Chem. Soc. 110 (1988) 3994-4002
48. Harayama H., Abe A., Sakado T., Kimura M., Fugami K., Tanaka S., and Tamaru Y. J. Org. Chem. 62 (1997) 2113-2122
49. Danishefsky S., Taniyama E., and Webb II R.R. Tetrahedron Lett. 24 (1983) 11-14
50. Lei A., and Lu X. Org. Lett. 2 (2000) 2699-2702
51. For related Pd-catalyzed carboamination reactions between aryl/alkenyl halides and unsaturated amines that generate pyrrolidine products, see:
52. Wolfe J.P. Eur. J. Org. Chem. (2007) 571-582
53. Ney J.E., and Wolfe J.P. Angew. Chem., Int. Ed. 43 (2004) 3605-3608
54. Beaudoin Bertrand M., and Wolfe J.P. Tetrahedron 61 (2005) 6447-6459
55. Yang Q., Ney J.E., and Wolfe J.P. Org. Lett. 7 (2005) 2575-2578
56. Ney J.E., Hay M.B., Yang Q., and Wolfe J.P. Adv. Synth. Catal. 347 (2005) 1614-1620
57. Bertrand M.B., and Wolfe J.P. Org. Lett. 8 (2006) 2353-2356
58. Bertrand M.B., Leathen M.L., and Wolfe J.P. Org. Lett. 9 (2007) 457-460
59. For related Pd-catalyzed carboamination or carboetherification reactions that generate tetrahydrofurans, isoxazolidines, or piperazines, see:
60. Hay M.B., Hardin A.R., and Wolfe J.P. J. Org. Chem. 70 (2005) 3099-3107
61. Hay M.B., and Wolfe J.P. J. Am. Chem. Soc. 127 (2005) 16468-16476
62. Hay M.B., and Wolfe J.P. Angew. Chem., Int. Ed. 46 (2007) 6492-6494
63. Nakhla J.S., and Wolfe J.P. Org. Lett. 9 (2007) 3279-3282 and references cited therein
64. A portion of this work has been previously communicated. See:. Fritz J.A., Nakhla J.S., and Wolfe J.P. Org. Lett. 8 (2006) 2531-2534
65. dppb=1,4-bis(diphenylphosphino)butane; dppe=1,2-bis(diphenylphosphino)ethane; dppf=1,1′-bis(diphenylphosphino)ferrocene; Xantphos=9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene; Nixantphos=4,6-bis(diphenylphosphino)phenoxazine.
66. With some catalyst systems the N-allylaniline side product underwent subsequent Pd-catalyzed N-arylation and/or was converted to mixtures of unidentified products.
67. This decomposition may involve deprotonation of urea followed by elimination and proton transfer to extrude the N-allylaniline and ethyl isocyanate. However, this has not been rigorously established experimentally. For related base-mediated cleavage of secondary carbamates, see:. Tom N.J., Simon W.M., Frost H.N., and Ewing M. Tetrahedron Lett. 45 (2004) 905-906
68. 8 at 110 °C led to complete isomerization to the internal alkene in <3 h.
69. Suh M.-J., Kim S.W., Beak S.I., Ha H.-J., and Lee W.K. Synlett (2004) 489-492
70. Kise N., Kashiwagi K., Watanabe M., and Yoshida J.-i. J. Org. Chem. 61 (1996) 428-429
71. Santos A.G., Pereira J., Afonso C.A.M., and Frenking G. Chem.-Eur. J. 11 (2005) 330-343
72. Seneci P., Caspani M., Ripamonti F., and Ciabatti R. J. Chem. Soc., Perkin Trans. 1 (1994) 2345-2351
73. Rondot C., and Zhu J. Org. Lett. 7 (2005) 1641-1644
74. In order to avoid competing reduction of the other aromatic moieties, it was necessary to quench the reduction at low temperature with diphenyl ether before addition of water. See:. Kim M.Y., Starrett Jr. J.E., and Weinreb S.M. J. Org. Chem. 46 (1981) 5383-5389
75. Quinet C., Jourdain P., Hermans C., Ates A., Lucas I., and Marko I.E. Tetrahedron 64 (2008) 1077-1087
76. Seayad J., Tillack A., Hartung C.G., and Beller M. Adv. Synth. Catal. 344 (2002) 795-813
77. Control experiments demonstrated that the hydroamination side reaction is base-mediated, and not Pd-catalyzed.
78. Link J.T. Org. React. 60 (2002) 157-534
79. Beletskaya I.P., and Cheprakov A.V. Chem. Rev. 100 (2000) 3009-3066
80. The relative stereochemistry of 47 was assigned via X-ray crystallographic analysis. Crystallographic data (excluding structure factors) for the structures in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC 604846. Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK, (fax: +44 (0)1223 336033) or e-mail: deposit@ccdc.cam.ac.uk).
81. The increased reactivity of cyclic alkenes relative to acyclic Z-disubstituted alkenes may be due to ring strain. For additional discussion on the effect of ring strain on reactivity in Pd-catalyzed reactions involving alkene insertion, see:
82. James D.E., and Stille J.K. J. Am. Chem. Soc. 98 (1976) 1810-1823
83. Larock R.C., and Baker B.E. Tetrahedron Lett. 29 (1988) 905-908
84. Ozawa F., Hayashi T., Koide H., and Yamamoto A. J. Chem. Soc., Chem. Commun. (1991) 1469-1470
85. 2Me-catalyzed carboaminations of N-(p-methoxyphenyl)-2-(cyclopent-2-enyl)ethylamine. See:. Ney J.E., and Wolfe J.P. J. Am. Chem. Soc. 127 (2005) 8644-8651
86. A small amount of N-(cyclohex-2-enyl)aniline was observed as a side product in this reaction.
87. Gillie A., and Stille J.K. J. Am. Chem. Soc. 102 (1980) 4933-4941
88. In analogy to related alkene insertions into Pd-C bonds, cyclization via a transition state in which the π-bond and the Pd-N bond are perpendicular is expected to be relatively high in energy. See Ref. 32.
89. Trost B.M., Sacchi K.L., Schroeder G.M., and Asakawa N. Org. Lett. 4 (2002) 3427-3430
90. Takeuchi R., Ue N., Tanabe K., Yamashita K., and Shiga N. J. Am. Chem. Soc. 123 (2001) 9525-9534
91. Green M.P., Prodger J.C., and Hayes C.J. Tetrahedron Lett. 43 (2002) 6609-6611
92. Schmidt B., Pohler M., and Costisella B. Tetrahedron 58 (2002) 7951-7958
93. Molander G.A., and Nichols P.J. J. Org. Chem. 61 (1996) 6040-6043
94. Molander G.A., and Romero J.A.C. Tetrahedron 61 (2005) 2631-2643
95. Nagashima H., Ozaki N., Ishii M., Seki K., Washiyama M., and Itoh K. J. Org. Chem. 58 (1993) 464-470
96. Barluenga J., Fananas F.J., Villamana J., and Yus M. J. Chem. Soc., Perkin Trans. 1 (1984) 2685-2692
97. Utsunomiya M., Miyamoto Y., Ipposhi J., Ohshima T., and Mashima K. Org. Lett. 9 (2007) 3371-3374
98. Pawlas J., Nakao Y., Kawatsura M., and Hartwig J.F. J. Am. Chem. Soc. 124 (2002) 3669-3679
99. Johns A.M., Utsunomiya M., Incarvito C.D., and Hartwig J.F. J. Am. Chem. Soc. 128 (2006) 1828-1839
100. Sadighi J.P., Singer R.A., and Buchwald S.L. J. Am. Chem. Soc. 120 (1998) 4960-4976