Palladium-catalyzed stereoselective intramolecular oxidative amidation of alkenes in the synthesis of 1,3- and 1,4-amino alcohols and 1,3-diamines

Chemistry - A European Journal

Volumn 20, Issue 17, 2014, Pages 4901-4905

  Malkov, Andrei V ^a   Lee, Darren S ^a   Barłõg, Maciej ^b   Elsegood, Mark R J ^a   Kočovský, Pavel ^c,d  

^a LOUGHBOROUGH UNIVERSITY   (United Kingdom)

^b TEXAS A AND M UNIVERSITY AT QATAR   (Qatar)

^c STOCKHOLM UNIVERSITY   (Sweden)

^d UNIVERSITY OF GLASGOW   (United Kingdom)

Author keywords

allylic compounds; amination; cyclization; homogeneous catalysis; palladium

Indexed keywords

AMINATION; AMINO ALCOHOLS; CATALYSIS; CYCLIZATION; PALLADIUM; REACTION KINETICS;

ALLYLIC AMIDATION; ALLYLIC COMPOUNDS; DIASTEREOSELECTIVITIES; HOMOGENEOUS CATALYSIS; MILD REACTION CONDITIONS; OXIDATIVE AMIDATION; PALLADIUM-CATALYZED; STEREOGENIC CENTERS;

STEREOSELECTIVITY;

EID: 84899461797     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201400123     Document Type: Article

References (101)

1. L. S. Hegedus, in Comprehensive Organic Synthesis Vol. 4 (Eds:, M. F. Semmelhack,), Pergamon Press, Elmsford, 1991, pp. 551-569
2. T. Hosokawa, S.-I. Murahashi, in Handbook of Organopalladium Chemistry for Organic Synthesis Vol. 2 (Eds:, E. Negishi, A. de Meijere,), John Wiley and Sons, NewYork, 2002, pp. 2169-2192
3. T. Hosokawa, in Handbook of Organopalladium Chemistry for Organic Synthesis Vol. 2 (Eds:, E. Negishi, A. de Meijere,), John Wiley and Sons, New York, 2002, pp. 2211-2225
4. G. Zeni, R. C. Larock, Chem. Rev. 2004, 104, 2285-2309
5. S. S. Stahl, Angew. Chem. 2004, 116, 3480-3501
6. Angew. Chem. Int. Ed. 2004, 43, 3400-3420
7. E. M. Beccalli, G. Broggini, M. Martinelli, S. Sottocornola, Chem. Rev. 2007, 107, 5318-5365
8. A. Minatti, K. Muñiz, Chem. Soc. Rev. 2007, 36, 1142-1152
9. V. Kotov, C. C. Scarborough, S. S. Stahl, Inorg. Chem. 2007, 46, 1910-1923
10. R. I. McDonald, G. Liu, S. S. Stahl, Chem. Rev. 2011, 111, 2981-3019
11. D. Schultz, J. Wolfe, Synthesis 2012, 44, 351-361
12. J. L. Roizen, M. E. Harvey, J. Du Bois, Acc. Chem. Res. 2012, 45, 911-922.
13. J. E. McMurry, P. Kočovský, Tetrahedron Lett. 1984, 25, 4187-4190
14. J. E. McMurry, P. Kočovský, Tetrahedron Lett. 1985, 26, 2171-2172
15. S. Hansson, A. Heumann, T. Rein, B. Åkermark, J. Org. Chem. 1990, 55, 975-984
16. S. E. Byström, E. M. Larsson, B. Åkermark, J. Org. Chem. 1990, 55, 5674-5675
17. E. M. Larsson, B. Åkermark, Tetrahedron Lett. 1993, 34, 2523-2526; for an overview, see
18. P. Kočovský, J. Organomet. Chem. 2003, 687, 256-268.
19. K. J. Fraunhoffer, C. M. White, J. Am. Chem. Soc. 2007, 129, 7274-7276
20. G. T. Rice, C. M. White, J. Am. Chem. Soc. 2009, 131, 11707-11711; for Ru and Rh-catalyzed intramolecular allylic C-H amidation, see
21. H. Lebel, K. Huard, S. Lectard, J. Am. Chem. Soc. 2005, 127, 14198-14199
22. D. N. Zalatan, J. Du Bois, J. Am. Chem. Soc. 2008, 130, 9220-9221
23. M. E. Harvey, D. G. Musaev, J. Du Bois, J. Am. Chem. Soc. 2011, 133, 17207-17216; for Fe-catalyzed intramolecular C-H amidation, see
24. S. M. Paradine, C. M. White, J. Am. Chem. Soc. 2012, 134, 2036-2039; for a related intramolecular nitroso-ene cyclization, see
25. C. P. Frazier, J. R. Engelking, J. Read de Alaniz, J. Am. Chem. Soc. 2011, 133, 10430-10433
26. D. Atkinson, M. A. Kabeshov, M. Edgar, A. V. Malkov, Adv. Synth. Catal. 2011, 353, 3347-3351.
27. For the recently observed dichotomy (C-N vs. C-O bond formation) in the Pd-catalyzed cyclization of homoallylic urea derivatives, rationalized by the switch between the C-H activation through a double bond isomerization versus π-allyl-Pd formation, see:, I. I. Strambeanu, C. R. White, J. Am. Chem. Soc. 2013, 135, 12032-12037.
28. R. A. T. M. van Benthem, H. Hiemstra, G. R. Longarela, W. N. Speckamp, Tetrahedron Lett. 1994, 35, 9281-9284
29. R. I. McDonald, S. S. Stahl, Angew. Chem. 2010, 122, 5661-5664
30. Angew. Chem. Int. Ed. 2010, 49, 5529-5532
31. A. Joosten, A. K. Å. Persson, R. Millet, M. T. Johnson, J.-E. Bäckvall, Chem. Eur. J. 2012, 18, 15151-15157
32. A. B. Weinstein, D. P. Schuman, Z. X. Tan, S. S. Stahl, Angew. Chem. 2013, 125, 12083-12086
33. Angew. Chem. Int. Ed. 2013, 52, 11867-11870.
34. A. V. Malkov, M. Barlõg, L. Miller-Potucká, M. A. Kabeshov, L. J. Farrugia, P. Kočovský, Chem. Eur. J. 2012, 18, 6873-6884; for an earlier work, see
35. P. Kočovský, M. Pour, J. Org. Chem. 1990, 55, 5580-5589; for a related carbonylation of terminal alkenes, see
36. A. V. Malkov, N. Derrien, M. Barłog, P. Kočovský, Chem. Eur. J. 2014, DOI:.
37. S. J. Buhrlage, B. B. Brennan, A. R. Minter, A. K. Mapp, J. Am. Chem. Soc. 2005, 127, 12456-12457
38. S. Hashiguchi, A. Kawada, H. Natsugari, J. Chem. Soc. Perkin Trans. 1 1991, 2435-2444
39. A. Vasella, R. Voeffray, J. Chem. Soc. Chem. Commun. 1981, 97-98.
40. R. W. Bates, K. Sa-Ei, Org. Lett. 2002, 4, 4225-4227
41. R. W. Bates, J. Boonsombat, Org. Biomol. Chem. 2005, 3, 520-523
42. R. W. Bates, J. Boonsombat, Y. Lu, J. A. Nemeth, K. Sa-Ei, P. Song, M. P. Cai, P. B. Cranwell, S. Winbush, Pure Appl. Chem. 2008, 80, 681-685
43. K. G. Dongol, B. Y. Tay, K. Xiang, Synth. Commun. 2006, 36, 1247-1257; see also
44. Y. Tamaru, M. Hojo, H. Higashimura, Z. Yoshida, J. Am. Chem. Soc. 1988, 110, 3994-4002.
45. K. G. Dongol, B. Y. Tay, Tetrahedron Lett. 2006, 47, 927-930
46. J. Peng, D. Jiang, W. Lin, Y. Chen, Org. Biomol. Chem. 2007, 5, 1391-1396
47. J. Peng, W. Lin, S. Yuan, Y. Chen, J. Org. Chem. 2007, 72, 3145-3148
48. M. B. Hay, J. P. Wolfe, Angew. Chem. 2007, 119, 6612-6614
49. Angew. Chem. Int. Ed. 2007, 46, 6492-6494
50. N. C. Giampietro, J. P. Wolfe, J. Am. Chem. Soc. 2008, 130, 12907-12911
51. G. S. Lemen, N. C. Giampietro, M. B. Hay, J. P. Wolfe, J. Org. Chem. 2009, 74, 2533-2540.
52. I. Starý, P. Kočovský, J. Am. Chem. Soc. 1989, 111, 4981-4982
53. I. Starý, J. Zajíček, P. Kočovský, Tetrahedron 1992, 48, 7229-7250
54. H. Kurosawa, S. Ogoshi, Y. Kawasaki, S. Murai, M. Miyoshi, I. Ikeda, J. Am. Chem. Soc. 1990, 112, 2813-2814
55. H. Kurosawa, H. Kajimaru, S. Ogoshi, H. Yoneda, K. Miki, N. Kasai, S. Murai, I. Ikeda, J. Am. Chem. Soc. 1992, 114, 8417-8424
56. 3-Mo complexes, see
57. D. Dvořák, I. Starý, P. Kočovský, J. Am. Chem. Soc. 1995, 117, 6130-6131
58. A. V. Malkov, L. Gouriou, G. C. Lloyd-Jones, I. Starý, V. Langer, P. Spoor, V. Vinader, P. Kočovský, Chem. Eur. J. 2006, 12, 6910-6929, and refs. given therein.
59. S. Murahashi, N. Koniya, Ruthenium-Catalyzed Oxidation for Organic Synthesis in Modern Oxidation Methods (Ed.:, J.-E. Bäckvall,), Wiley-VCH, Weinheim 2010, p. 241-275
60. J.-E. Bäckvall, Selective Oxidation of Amines and Sulfides in Modern Oxidation Methods (Ed.:, J.-E. Bäckvall,), Wiley-VCH, Weinheim 2010, p. 277-313.
61. J. Tsuji, Synthesis 1984, 369-384
62. J. M. Takacs, X. T. Jiang, Curr. Org. Chem. 2003, 7, 369-396
63. C. N. Cornell, M. S. Sigman, Inorg. Chem. 2007, 46, 1903-1909
64. J. A. Keith, P. M. Henry, Angew. Chem. 2009, 121, 9200-9212
65. Angew. Chem. Int. Ed. 2009, 48, 9038-9049.
66. H. Mimoun, I. Serre de Roch. L. Sajus, Bull. Soc. Chim. Fr. 1969, 1481
67. E. Vedejs, J. Am. Chem. Soc. 1974, 96, 5944-5946.
68. Z. Lu, S. S. Stahl, Org. Lett. 2012, 14, 1234-1237
69. T. Diao, P. White, I. Guzei, S. S. Stahl, Inorg. Chem. 2012, 51, 11898-11909.
70. B. Janza, A. Studer, J. Org. Chem. 2005, 70, 6991-6994
71. A. Barco, N. Baricordi, S. Benetti, C. De Risi, G. P. Pollinib, V. Zanirato, Tetrahedron 2007, 63, 4278-4283
72. R. W. Bates, R. H. Snell, S. Winbush, Synlett 2008, 1042-1044
73. R. L. LaLonde, Z. J. Wang, M. Mba, A. D. Lackner, F. D. Toste, Angew. Chem. 2010, 122, 608-611
74. Angew. Chem. Int. Ed. 2010, 49, 598-601.
75. J. Nokami, K. Nomiyama, S. Matsuda, N. Imai, K. Kataoka, Angew. Chem. 2003, 115, 1311-1314
76. Angew. Chem. Int. Ed. 2003, 42, 1273-1276
77. T.-P. Loh, C.-L. K. Lee, K.-T. Tan, Org. Lett. 2002, 4, 2985-2987
78. A. V. Malkov, M. Bell, P. Ramírez-Lõpez, L. Biedermannová, L. Rulíšek, L. Dufková, M. Kotora, F. Zhu, P. Kočovský, J. Am. Chem. Soc. 2008, 130, 5341-5348
79. A. V. Malkov, M. A. Kabeshov, M. Barłõg, P. Kočovský, Chem. Eur. J. 2009, 15, 1570-1573
80. A. V. Malkov, M. Barłõg, Y. Jewkes, J. Mikušek, P. Kočovský, J. Org. Chem. 2011, 76, 4800-4804
81. C. A. Incerti-Pradillos, M. A. Kabeshov, A. V. Malkov, Angew. Chem. 2013, 125, 5446-5449
82. Angew. Chem. Int. Ed. 2013, 52, 5338-5341
83. A. V. Malkov, S. Stončius, M. Bell, F. Castelluzzo, P. Ramírez-Lõpez, L. Biedermannová, L. Rulíšek, V. Langer, P. Kočovský, Chem. Eur. J. 2013, 19, 9167-9185.
84. V. E. Marquez, M. Lim, Med. Res. Rev. 1986, 6, 1-40
85. J. Štambaský, M. Hocek, P. Kočovský, Chem. Rev. 2009, 109, 6729-6764.
86. For the method, see ref. [6a] and:, S. Cicchi, A. Goti, A. Brandi, A. Guarna, F. De Sarlo, Tetrahedron Lett. 1990, 31, 3351-3354.
87. P. Kočovský, Tetrahedron Lett. 1986, 27, 5521
88. P. Kočovský, I. Starý, J. Org. Chem. 1990, 55, 3236-3243; for the first example of carbamate stereocontrol in cyclic olefins, see
89. K. Ponsold, G. Schubert, M. Wunderwald, D. Tresselt, J. Prakt. Chem. 1981, 323, 819-828; for the first example of a stereocontrolled epoxidation of cycloalkene tosylamides, see
90. J.-E. Bäckvall, K. Oshima, R. E. Palermo, K. B. Sharpless, J. Org. Chem. 1979, 44, 1953-1957.
91. E. D. Mihelich, Tetrahedron Lett. 1979, 20, 4729
92. B. E. Rossiter, T. R. Verhoeven, K. B. Sharpless, Tetrahedron Lett. 1979, 20, 4733; for overviews, see
93. P. Kočovský, F. Tureček, J. Hájí ček, Synthesis of Natural Products: Problems of Stereoselectivity Vol. 2, CRC Press, Boca Raton, Florida 1986, pp. 138-143
94. A. H. Hoveyda, D. A. Evans, G. C. Fu, Chem. Rev. 1993, 93, 1307-1370.
95. J. Cornil, A. Guériont, S. Reymond, J. Cossy, J. Org. Chem. 2013, 78, 10273-10287; for a related activation with Pd and/or Mo, see
96. I. Starý, I. Stará, P. Kočovský, Tetrahedron Lett. 1993, 34, 179-182
97. A. V. Malkov, I. R. Baxendale, D. Dvořák, D. J. Mansfield, P. Kočovský, J. Org. Chem. 1999, 64, 2737-2750
98. A. V. Malkov, S. L. Davis, I. R. Baxendale, W. L. Mitchell, P. Kočovský, J. Org. Chem. 1999, 64, 2751-2764
99. A. V. Malkov, P. Spoor, V. Vinader, P. Kočovský, J. Org. Chem. 1999, 64, 5308-5311.
100. APEX 2 and SAINT (2009) software for CCD diffractometers. Bruker AXS Inc., Madison, USA.
101. G. M. Sheldrick, Acta Crystallogr. 2008, A64, 112-122.