Pd-catalyzed intramolecular amidation of 2-(buta-1,3-dienyl)phenylcarbamoyl chloride: a concise synthesis of spiro[indoline-3,3′-pyrrolidine]

Tetrahedron Letters

Volumn 50, Issue 21, 2009, Pages 2589-2592

  Kamisaki, Haruhi ^a   Yasui, Yoshizumi ^b   Takemoto, Yoshiji ^a  

^a KYOTO UNIVERSITY   (Japan)

^b TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

2 (BUTA 1,3 DIENYL)PHENYLCARBAMOYLCHLORIDE; CARBAMIC ACID DERIVATIVE; CHLORIDE; PALLADIUM; PYRROLIDINE DERIVATIVE; SPIRO(INDOLINE 3,3' PYRROLIDINE); UNCLASSIFIED DRUG;

AMIDATION; ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; SYNTHESIS;

EID: 64149128578     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.03.100     Document Type: Article

References (65)

1. For a review, see:. Galliford C.V., and Sheidt K.A. Angew. Chem., Int. Ed. 46 (2007) 8748
2. For recent examples, see:. Kolackowski M., Nowak M., Pawlowski M., and Bojarski A.J. J. Med. Chem. 49 (2006) 6732
3. Kato H., Yoshida T., Tokue T., Nojiri Y., Hirota H., Ohta T., Williams R.M., and Tsukamoto S. Angew. Chem., Int. Ed. 46 (2007) 2254
4. Uddin M.K., Reignier S.G., Coulter T., Montalbetti C., Grånäs C., Butcher S., Krog-Jensen C., and Felding J. Bioorg. Med. Chem. Lett. 17 (2007) 2854
5. Stevens F.C., Bloomquist W.E., Borel A.G., Cohen M.L., Droste C.A., Heiman M.L., Kriauciunas A., Shall D.J., Tinsley F.C., and Jesudason C.D. Bioorg. Med. Chem. Lett. 17 (2007) 6270
6. Syntheses:. Pellegrim C., eber M., and Borschberg H.-J. Helv. Chim. Acta. 79 (1996) 151
7. Miyake F.Y., Yakushijin K., and Home D.A. Org. Lett. 6 (2004) 711
8. Isolation:. Cui C.B., Kakeya H., and Osada H. J. Antibiot. 49 (1996) 832
9. Cui C.B., Kakeya H., and Osada H. Tetrahedron 52 (1996) 12651
10. Syntheses:. Trost B.M., and Stiles D.T. Org. Lett. 9 (2007) 2763 and references sited therein
11. Isolation. Elderfield R.C., and Gilman R.E. Phytochemistry 11 (1972) 339
12. Ghedira K., Hanrot M.Z., Richard B., Massiot G., Oliver L.L.M., Sevener T., and Goh S.H. Phytochemistry 27 (1988) 3955
13. Wong W.H., Lim P.B., and Chuah C.H. Phytochemistry 41 (1996) 313
14. Biomimetic transformations:. Garnick R.L., and LeQuensne P.W. J. Am. Chem. Soc. 100 (1978) 4213
15. Syntheses. Yang J., Wearing X.Z., Quesne P.W.L., Deschamps J.R., and Cook J.M. J. Nat. Prod. 71 (2008) 1431
16. Wearing X.Z., and Cook J.M. Org. Lett. 4 (2002) 4237 and references sited therein
17. For a review, see:. Marti C., and Carreira E.M. Eur. J. Org. Chem. (2003) 2209
18. Recent example, see:. Trost B.M., and Brennan M.K. Org. Lett. 8 (2006) 2027 and Refs. 3(c), 4(f)
19. Lizos D., Tripoli R., and Murphy J.A. Chem. Commun. (2001) 2732
20. Synthesis of spirotriprostatin:. Overman L.E., and Rosen M.D. Angew. Chem., Int. Ed. 39 (2000) 4596
21. Synthesis of gelsemines:. Earley W.G., Oh T., and Overman L.E. Tetrahedron Lett. 29 (1988) 3785
22. Madin A., O'Donnell C.J., Oh T., Old D.W., Overman L.E., and Sharp M.J. Angew. Chem., Int. Ed. 38 (1999) 2934
23. Beyersbergen van Henegouwen W.G.B., Fieseler R.M., Rutjes F., and Hiemstra H. Angew. Chem., Int. Ed. 38 (1999) 2214
24. Beyersbergen van Henegouwen W.G.B., Fieseler R.M., Rutjes F., and Hiemstra H. J. Org. Chem. 65 (2000) 8317
25. For a review, see:. Yasui Y., and Takemoto Y. Chem. Rec. 8 (2008) 386
26. Pd-catalyzed cyanoamidation:. Kobayashi Y., Kamisaki H., Yanada R., and Takemoto Y. Org. Lett. 8 (2006) 2711
27. Kobayashi Y., Kamisaki H., Takeda H., Yasui Y., Yanada R., and Takemoto Y. Tetrahedron 63 (2007) 2978
28. Yasui Y., Kamisaki H., and Takemoto Y. Org. Lett. 10 (2008) 3303
29. Rh-catalyzed Intramolecular hydroamidation of alkynes:. Kobayashi Y., Kamisaki H., Yanada K., Yanada R., and Takemoto Y. Tetrahedron Lett. 46 (2005) 7549
30. Pd-catalyzed Heck-type reaction of chloroformamides:. Yasui Y., Takeda H., and Takemoto Y. Chem. Pharm. Bull. 56 (2008) 1567
31. Heck R.F. J. Am. Chem. Soc. 85 (1963) 3381
32. Robinson S.D., and Shaw B.L. J. Chem. Soc. (1963) 4806
33. Rowe R.M., and White D.A. J. Chem. Soc. (1967) 1451
34. For a review, see:. Andersson P.G., and Backvall J.-E. In: Negishi E. (Ed). Handbook of Organopalladium Chemsitry for Organic Synthesis (2002), John Wiley & Sons 1859-1874
35. Vackvall J.-E. In: Diederich F., and Stang P.J. (Eds). Metal-catalyzed Cross-coupling Reactions (1998), Wiley-VCH, Weinheim 339-385
36. Balme G., Bossharth E., and Monterio N. Eur. J. Org. Chem. (2003) 4101
37. Addition of N-nucleophles to conjugated dienes catalyzed by palladium(0), see:. Patel B.A., Dickerson J.E., and Heck R.F. J. Org. Chem. 43 (1978) 5018
38. Stakem F.G., and Heck R.F. J. Org. Chem. 45 (1980) 3584
39. O'Connor J.M., Stallman B.J., Clark W.G., Shu A.Y.L., and Spada R.E. J. Org. Chem. 48 (1983) 807
40. Shi L., Narula C.K., Mak K.T., Kao L., Xu Y., and Heck R.F. J. Org. Chem. 48 (1983) 3894
41. Mitsudo T., Fischetti W., and Heck R.F. J. Org. Chem. 49 (1984) 1640
42. Larock R.C., Berrios-Pena N., and Narayanan K. J. Org. Chem. 55 (1990) 3447
43. Back T.G., and Bethell R.J. Tetrahedron Lett. 39 (1998) 5463
44. Flubacher D., and Helmchen G. Tetrahedron Lett. 40 (1999) 3867
45. Xie X., and Lu X. Tetrahedron Lett. 40 (1999) 8415
46. Currently, the mechanism of the generation of 2a′ is not clear.
47. Yasui Y., Tsuchida S., Miyabe H., and Takemoto Y. J. Org. Chem. 72 (2007) 5898
48. For a review, see:. Kuniyasu H., and Kambe N. Chem. Lett. 35 (2006) 1320
49. Recently, various acylation reactions of unsaturated bonds were investigated, see: thioacylation,. Minami Y., Kuniyasu H., and Kambe N. Org. Lett. 10 (2008) 2469
50. Kuniyasu H., Kato T., Asano S., Ye J.-H., Ohmori T., Morita M., Hiraike H., Fujiwara S., Terao J., Kurosawa H., and Kambe N. Tertahedron Lett. 47 (2006) 1141
51. Selenoacylation:. Toyofuku M., Fujiwara S., Shin-ike T., Kuniyasu H., and Kambe N. J. Am. Chem. Soc. 127 (2005) 9706
52. Toyofuku M., Murase E., Fujiwara S., Shin-ike T., Kuniyasu H., and Kambe N. Org. Lett. 10 (2008) 3957
53. Recently, interesting vinylchalcogenation was investigated, see:. Toyofuku M., Fujiwara S., Shin-ike T., Kuniyasu H., and Kambe N. J. Am. Chem. Soc. 130 (2008) 10504
54. Cyanocarbonylation:. Nozaki K., Sato N., and Takaya H. J. Org. Chem. 59 (1994) 2679
55. Nozaki K., Sato N., and Takaya H. Bull. Chem. Soc. Jpn. 69 (1996) 1629
56. Nishihara Y., Inoue Y., Itazaki M., and Takagi K. Org. Lett. 7 (2005) 2639
57. Nishihara Y., Inoue Y., Izawa S., Miyasaka M., Tanemura K., Nakajima K., and Takagi K. Tetrahedron 62 (2006) 9872
58. Nakao Y., Hirata Y., and Hiyama T. J. Am. Chem. Soc. 128 (2006) 7420 and our examples, see ref.8
59. Mandai T., Matsumoto T., Kawada M., and Tsuji J. J. Org. Chem. 57 (1992) 1326
60. Hydrogenation of π-allyl Pd complexes, see:. Tsuji M., and Mandai T. Synthesis (1996) 1
61. Pd(II)-catalyzed oxidation of alcohols, see:. Nishimura T., Onoue T., Ohe K., and Uemura S. J. Org. Chem. 64 (1999) 6750
62. Pd(0)-catalyzed allylic reduction with polymethylhydrosiloxane (PMHS), see:. Greenspoon N., and Keinan E. J. Org. Chem. 53 (1988) 3723
63. Keinan E., and Greenspoon N. J. Org. Chem. 48 (1983) 3545
64. Pd-catalyzed cyclization of carbamoyl chlorides via anion capture processes using organostannanes and organoboranes, see:. Anwar J., Fielding M.R., Grigg R., Sridharan V., and Urch C.J. J. Organomet. Chem. 691 (2006) 1476
65. Synthesis of (Z)-6-tert-butyldimethylsilyloxy-4-trimethylstannyl-1,3-hexadiene, see:. Piers E., and Tillyer R.D. Can. J. Chem. 74 (1996) 2048