Modular synthesis of chiral β-diketiminato-type ligands containing 2-oxazoline moiety via palladium-catalyzed amination

Synthesis

Volumn , Issue 16, 2011, Pages 2609-2618

  Binda, Pascal I ^a   Abbina, Srinivas ^a   Du, Guodong ^a  

^a UNIVERSITY OF NORTH DAKOTA   (United States)

Author keywords

amination; chiral auxiliaries; chirality; ligands; nitrogen; palladium

Indexed keywords

2-OXAZOLINE; AMINATION REACTION; ASYMMETRIC CATALYSIS; CHIRAL AUXILIARIES; CHIRAL BUILDING BLOCKS; CHIRAL OXAZOLINES; HIGH YIELD; MODULAR APPROACH; MODULAR SYNTHESIS; OXAZOLINES; PALLADIUM-CATALYZED AMINATION; POTENTIAL APPLICATIONS; PRIMARY AMINES;

AMIDES; AMINES; CATALYSIS; LAKES; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

LIGANDS;

2 OXAZOLINE DERIVATIVE; 4,5 DIHYDRO 2 [2' (2,6 DIISOPROPYLANILINO)PHENYL] 4 ISOBUTYLOXAZOLINE DERIVATIVE; 4,5 DIHYDRO 2 [2' (2,6 DIISOPROPYLANILINO)PHENYL] 4 ISOPROPYLOXAZOLINE DERIVATIVE; 4,5 DIHYDRO 2 [2' (2,6 DIISOPROPYLANILINO)PHENYL] 4 PHENYLOXAZOLINE DERIVATIVE; 4,5 DIHYDRO 2 [2' (2,6 DIISOPROPYLANILINO)PHENYL] 4 SEC BUTYLOXAZOLINE DERIVATIVE; 4,5 DIHYDRO 2 [2' (2,6 DIMETHYLANILINO)PHENYL] 4 ISOBUTYLOXAZOLINE DERIVATIVE; 4,5 DIHYDRO 2 [2' (2,6 DIMETHYLANILINO)PHENYL] 4 ISOPROPYLOXAZOLINE DERIVATIVE; 4,5 DIHYDRO 2 [2' (2,6 DIMETHYLANILINO)PHENYL] 4 PHENYLOXAZOLINE DERIVATIVE; 4,5 DIHYDRO 2 [2' (2,6 DIMETHYLANILINO)PHENYL] 4 SEC BUTYLOXAZOLINE DERIVATIVE; 4,5 DIHYDRO 2 [2' (ALPHA METHYLBENZYLAMINO)PHENYL] 4 ISOBUTYLOXAZOLINE DERIVATIVE; 4,5 DIHYDRO 2 [2' (ALPHA METHYLBENZYLAMINO)PHENYL] 4 ISOPROPYLOXAZOLINE DERIVATIVE; 4,5 DIHYDRO 2 [2' (ALPHA METHYLBENZYLAMINO)PHENYL] 4 PHENYLOXAZOLINE DERIVATIVE; 4,5 DIHYDRO 2 [2' (ALPHA METHYLBENZYLAMINO)PHENYL] 4 SEC BUTYLOXAZOLINE DERIVATIVE; 4,5 DIHYDRO 2 [2' (BENZAMIDO)PHENYL] 4 ISOBUTYLOXAZOLINE DERIVATIVE; 4,5 DIHYDRO 2 [2' (BENZAMIDO)PHENYL] 4 ISOPROPYLOXAZOLINE DERIVATIVE; 4,5 DIHYDRO 2 [2' (BENZAMIDO)PHENYL] 4 PHENYLOXAZOLINE DERIVATIVE; 4,5 DIHYDRO 2 [2' (BENZAMIDO)PHENYL] 4 SEC BUTYLOXAZOLINE DERIVATIVE; 4,5 DIHYDRO 2 [2' (TERT BUTYLSULFINAMIDO)PHENYL] 4 SEC BUTYLOXAZOLINE DERIVATIVE; 4,5 DIHYDRO 2 [2' [1 (1 NAPHTHYL)ETHYLAMINO]PHENYL] 4 ISOBUTYLOXAZOLINE DERIVATIVE; 4,5 DIHYDRO 2 [2' [1 (1 NAPHTHYL)ETHYLAMINO]PHENYL] 4 ISOPROPYLOXAZOLINE DERIVATIVE; 4,5 DIHYDRO 2 [2' [1 (1 NAPHTHYL)ETHYLAMINO]PHENYL] 4 PHENYLOXAZOLINE DERIVATIVE; 4,5 DIHYDRO 2 [2' [1 (1 NAPHTHYL)ETHYLAMINO]PHENYL] 4 SEC BUTYLOXAZOLINE DERIVATIVE; AMIDE; AMINE; AROMATIC AMINE; OXAZOLINE DERIVATIVE; PALLADIUM; SULFINAMIDE; TERT BUTYLSULFINAMIDE; UNCLASSIFIED DRUG;

AMINATION; ARTICLE; CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; CHIRALITY; CROSS COUPLING REACTION;

EID: 80051551996     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0030-1260124     Document Type: Article

References (81)

1. Walsh P J., Kozlowski M C., Fundamentals in Asymmetric Catalysis USB Sausalito / CA 2008
2. Jacobsen E N., Pfaltz A, Yamamoto H, Comprehensive Asymmetric Catalysi s Springer Heidelberg 1999
3. Martin R, Buchwald S L., Acc. Chem. Res. 2008 41 1461
4. Heitbaum M, Glorius F, Escher I, Angew. Chem. Int. Ed. 2006 45 4732
5. Hoveyda A H., Hird A W., Kacprzynski M A., Chem. Commun. 2004 1779
6. Lu Y, Johnstone T C., Arndtsen B A., J. Am. Chem. Soc. 2009 131 11284
7. Shi B.-F, Maugel N, Zhang Y.-H, Yu J.-Q, Angew. Chem. Int. Ed. 2008 47 4882
8. Blaser H.-U, Pugin B, Spindler F, Thommen M, Acc. Chem. Res. 2007 40 1240
9. Cesar V, Bellemin-Laponnaz S, Wadepohl H, Gade L H., Chem. Eur. J. 2005 11 2862
10. Pfaltz A, Drury W J. III, Proc. Natl. Acad. Sci. U.S.A. 2004 101 5723
11. Bourget-Merle L, Lappert M F., Severn J R., Chem. Rev. 2002 102 3031
12. Bourget-Merle L, Cheng Y, Doyle D J., Hitchcock P B., Khvostov A V., Lappert M F., Protchenko V, Wei X, ACS Symposium Series 2006 917 192
13. Holland P L., Acc. Chem. Res. 2008 41 905
14. Mindiola D J., Comments Inorg. Chem. 2008 29 73
15. Chomitz W A., Arnold J, Chem. Eur. J. 2009 15 2020
16. Badiei Y M., Dinescu A, Dai X, Palomino R M., Heinemann F W., Cundari T R., Warren T H., Angew. Chem. Int. Ed. 2008 47 9961
17. Eckert N A., Bones E M., Lachicotte R J., Holland P L., Inorg. Chem. 2003 42 1720
18. Cheng M, Moore D R., Reczek J J., Chamberlain B M., Lobkovsky E B., Coates G W., J. Am. Chem. Soc. 2001 123 8738
19. Champouret Y, Baisch U, Poli R, Tang L, Conway J L., Smith K M., Angew. Chem. Int. Ed. 2008 47 6069
20. Lazarov B B., Hampel F, Hultzsch K C., Doz P, [nl]Z. Anorg. Allg. Chem. 2007 633 2367
21. Vollmerhaus R, Rahim M, Tomaszewski R, Xin S, Taylor N J., Collins S, Organometallics 2000 19 2161
22. Li J, Tian D, Song H, Wang C, Zhu X, Cui C, Cheng J.-P, Organometallics 2008 27 1605
23. Chen C.-T, Chan C.-Y, Huang C.-A, Chen M.-T, Peng K.-F, Dalton Trans. 2007 4073
24. Badiei Y M., Krishnaswamy A, Melzer M M., Warren T H., J. Am. Chem. Soc. 2006 128 15056
25. Gao H, Guo W, Bao F, Gui G, Zhang J, Zhu F, Wu Q, Organometallics 2004 23 6273
26. Luo F.-T, Ravi V K., Xue C, Tetrahedron 2006 62 9365
27. Gomez M, Jansat S, Muller G, Aullon G, Maestro M A., Eur. J. Inorg. Chem. 2005 4341
28. Pfaltz A, J. Heterocycl. Chem. 1999 36 1437
29. Cortright S B., Johnston J N., Angew. Chem. Int. Ed. 2002 41 345
30. Drouin F, Oguadinma P O., Whitehouse T J. J., Prudhomme R E., Schaper F, Organometallics 2010 29 2139
31. El-Zoghbi I, Latreche S, Schaper F, Organometallics 2010 29 1551
32. Oguadinma P O., Schaper F, Organometallics 2009 28 4089
33. Cheng M, Darling N A., Lobkovsky E B., Coates G W., Chem. Commun. 2000 2007
34. Bertilsson S K., Tedenborg L, Alonso D A., Anderson P G., Organometallics 1999 18 1281
35. Wan Z.-K, Choi H.-w, Kang F.-A, Nakajima K, Demeke D, Kishi Y, Org. Lett. 2002 4 4431
36. Brunner H, Rahman A F. M., Z. Naturforsch., B: J. Chem. Sci. 1983 38 1332
37. Zhou Y.-B, Tang F.-Y, Xu H.-D, Wu X.-Y, Ma J.-A, Zhou Q.-L, Tetrahedron: Asymmetry 2002 13 469
38. Buch F, Harder S, Z. Naturforsch., B: J. Chem. Sci. 2008 63 169
39. Köhler V, Mazet C, Toussaint A, Kulicke K, Häussinger D, Neuburger M, Schaffner S, Kaiser S, Pfaltz A, Chem. Eur. J. 2008 14 8530
40. Mazet C, Köhler V, Roseblade S, Toussaint A, Pfaltz A, Chimia 2006 60 195
41. End N, Macko L, Zehnder M, Pfaltz A, Chem. Eur. J. 1998 4 818
42. Chen Y, Ruppel J V., Zhang X P., [nl]J. Am. Chem. Soc. 2007 129 12074
43. Pfaltz A, Acc. Chem. Res. 1993 26 339
44. Leutenegger U, Madin A, Pfaltz A, Angew. Chem., Int. Ed. Engl. 1989 28 60
45. Dagorne S, Bellemin-Laponnaz S, Maisse-Francois A, Eur. J. Inorg. Chem. 2007 913
46. Sibi M P., Asano Y, J. Am. Chem. Soc. 2001 123 9708
47. Mueller D, Umbricht G, Weber B, Pfaltz A, Helv. Chim. Acta 1991 74 232
48. Lowenthal R E., Abiko A, Masamune S, Tetrahedron Lett. 1990 31 6005
49. Luesse S B., Counceller C M., Wilt J C., Perkins B R., Johnston J N., Org. Lett. 2008 10 2445
50. Cortright S B., Huffman J C., Yoder R A., Coalter J N. III, Johnston J N., Organometallics 2004 23 2238
51. Cortright S B., Yoder R A., Johnston J N., Heterocycles 2004 62 223
52. Kawabata T, Jiang C, Hayashi K, Tsubaki K, Yoshimura T, Majumdar S, Sasamori T, Tokitoh N, [nl]J. Am. Chem. Soc. 2009 131 54
53. Barrett A G. M., Gray A A., Hill M S., Hitchcock P B., Procopiou P A., White A J. P., Inorg. Chem. 2006 45 3352
54. Schneider N, Bellemin-Laponnaz S, Wadepohl H, Gade L H., Eur. J. Inorg. Chem. 2008 5587
55. Hargaden G C., McManus H A., Cozzi P G., Guiry P J., Org. Biomol. Chem. 2007 5 763
56. Lu S.-F, Du D.-M, Zhang S.-W, Xu J, Tetrahedron: Asymmetry 2004 15 3433
57. Inoue M, Nakada M, Org. Lett. 2004 6 2977
58. Inoue M, Suzuki T, Nakada M, J. Am. Chem. Soc. 2003 125 1140
59. Miller J J., Rajaram S, Pfaffenroth C, Sigman M S., Tetrahedron 2009 65 3110
60. McManus H A., Cozzi P G., Guiry P J., Adv. Synth. Catal. 2006 348 551
61. McManus H, Guiry P J., Chem. Rev. 2004 104 4151
62. Hargaden G, Guiry P J., Chem. Rev. 2009 109 2505
63. Zhou Q.-L, Pfaltz A, Tetrahedron 1994 50 4467
64. Schwekendiek K, Glorius F, Synthesis 2006 2996
65. See Supporting Information for more details.
66. Surry D S., Buchwald S L., Angew. Chem. Int. Ed. 2008 47 6338
67. Surry D S., Buchwald S L., Chem. Sci. 2010 1 13
68. Wolfe J P., Wagaw S, Buchwald S L., J. Am. Chem. Soc. 1996 118 7215
69. Li J J., Wang Z, Mitchell L H., J. Org. Chem. 2007 72 3606
70. Wolfe J P., Buchwald S L., J. Org. Chem. 2000 65 1144
71. Chen Y, Fields K B., Zhang X P., J. Am. Chem. Soc. 2004 126 14718
72. Bolm C, Hildebrand J P., J. Org. Chem. 2000 65 169
73. Kamikawa K, Sugimoto S, Uemura M, J. Org. Chem. 1998 63 8407
74. McManus H A., Guiry P J., J. Org. Chem. 2002 67 8566
75. Coeffard V, Muller-Bunz H, Guiry P J., Org. Biomol. Chem. 2009 7 1723
76. Doherty S, Knight J G., Smyth C H., Sore N T., Rath R K., McFarlane W, Harrington R W., Clegg W, Organometallics 2006 25 4341
77. McKeon S, Muller-Benz H, Guiry P J., Eur. J. Org. Chem. 2009 4833
78. Xie X, Zhang T Y., Zhang Z, J. Org. Chem. 2006 71 6522
79. Gao G.-Y, Chen Y, Zhang X P., Org. Lett. 2004 6 1837
80. Tobak M T., Herbage M A., Ellman J A., Chem. Rev. 2010 110 3600
81. Hargaden G C., Muller-Bunz H, Guiry P J., Eur. J. Org. Chem. 2007 4235