Chiral N-heterocyclic carbene-copper(I)-catalyzed asymmetric allylic arylation of aliphatic allylic bromides: Steric and electronic effects on γ-selectivity

Journal of Organic Chemistry

Volumn 76, Issue 5, 2011, Pages 1398-1408

  Selim, Khalid B ^a   Nakanishi, Hirotsugu ^b   Matsumoto, Yasumasa ^b   Yamamoto, Yasutomo ^c   Yamada, Ken Ichi ^b   Tomioka, Kiyoshi ^b,c  

^a University of Mansoura   (Egypt)

^b KYOTO UNIVERSITY   (Japan)

^c DOSHISHA WOMEN'S COLLEGE OF LIBERAL ARTS   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ARYL GROUP; ARYLATIONS; CARBENE LIGANDS; CHIRAL N-HETEROCYCLIC CARBENES; ELECTRON DEFICIENCY; ELECTRON-DEFICIENT; ELECTRONIC EFFECTS; GRIGNARD REAGENT; REDUCTIVE ELIMINATION; STERIC HINDRANCES;

AROMATIC COMPOUNDS; BROMINE COMPOUNDS; CARBON INORGANIC COMPOUNDS; CATALYSIS; COPPER; ISOMERS;

LIGANDS;

ALIPHATIC COMPOUND; BROMINE DERIVATIVE; CARBENE; COPPER ION; GRIGNARD REAGENT;

ARTICLE; ARYLATION; CATALYSIS; CATALYST; CHIRALITY; ELECTRON; ENANTIOSELECTIVITY; STEREOCHEMISTRY;

CATALYSIS; COPPER; ELECTRONS; HETEROCYCLIC COMPOUNDS; HYDROCARBONS, BROMINATED; METHANE; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; STEREOISOMERISM;

EID: 79952141058     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo102386s     Document Type: Article

References (56)

1. Trost, B. M.; Lee, C. In Catalytic Asymmetric Synthesis, 2 nd ed.; Ojima, I., Ed.; Wiley: New York, 2000; p 593.
2. Helmchen, G. In Asymmetric Synthesis-The Essentials; Christmann, M., Bräse, S., Eds.; Wiley-VCH: Weinheim, Germany, 2007; pp 95 -99.
3. Karlström, A. S. E.; Bäckvall, J. E. In Modern Organocopper Chemistry; Krause, N., Ed.; Wiley-VCH: Weinheim, Germany, 2001; p 259.
4. Recent reviews in Cu-catalyzed asymmetric allylic substitution: Alexakis, A.; Bäckvall, J. E.; Krause, N.; Pàmies, O.; Diéguez, M. Chem. Rev. 2008, 108, 2796-2823
5. Harutyunyan, S. R.; den Hartog, T.; Geurts, K.; Minnaard, A. J.; Feringa, B. L. Chem. Rev. 2008, 108, 2824-2852
6. Falciola, C.; Alexakis, A. Eur. J. Org. Chem. 2008, 3765-3780
7. Alexakis, A.; Malan, C.; Lea, L.; Tissot-Croset, K.; Polet, D.; Falciola, C. Chimia 2006, 60, 124-130
8. Yorimitsu, H.; Oshima, K. Angew. Chem., Int. Ed. 2005, 44, 4435-4439
9. Kar, A.; Argade, N. P. Synthesis 2005, 2995-3022
10. Hoveyda, A. H.; Hird, A. W.; Kacprzynski, M. A. Chem. Commun. 2004, 1779-1785
11. Copper-mediated γ-selective allylic substitution using directing leaving groups: Breit, B.; Schmidt, Y. Chem. Rev. 2008, 108, 2928-2951
12. Kiyotsuka, Y.; Kobayashi, Y. J. Org. Chem. 2009, 74, 7489-7495, and references therein
13. Tseng, C. C.; Paisley, S. D.; Goering, H. L. J. Org. Chem. 1986, 51, 2884-2891
14. Bäckvall, J. E.; Persson, E. S. M.; Bombrun, A. J. Org. Chem. 1994, 59, 4126-4130
15. A maximum of 30% ee has been achieved in Cu-catalyzed AAAr using aryl Grignard reagent: Meuzelaar, G. J.; Karlstrom, A. S. E.; Van Klaveren, M.; Persson, E. S. M.; Del Villar, A.; van Koten, G.; Bäckvall, J. E. Tetrahedron 2000, 56, 2895-2903
16. Alexakis, A.; Malan, C.; Lea, L.; Benhaim, C.; Fournioux, X. Synlett 2001, 927-930
17. Seo, H.; Hirsch-Weil, D.; Abboud, K. A.; Hong, S. J. Org. Chem. 2008, 73, 1983-1986
18. Falciola, C. A.; Alexakis, A. Chem.-Eur. J. 2008, 14, 10615-10627
19. Kacprzynski, M. A.; May, T. L.; Kazane, S. A.; Hoveyda, A. H. Angew. Chem., Int. Ed. 2007, 46, 4554-4558
20. Gao, F.; Lee, Y.; Mandai, K.; Hoveyda, A. H. Angew. Chem., Int. Ed. 2010, 49, 8370-8374
21. Lee, Y.; Akiyama, K.; Gillingham, D. G.; Brown, M. K.; Hoveyda, A. H. J. Am. Chem. Soc. 2008, 130, 446-447
22. Ir-catalyzed AAAr with arylzinc reagents in high enantioselectivity but moderate regioselectivity: Alexakis, A.; El Hajjaji, S.; Polet, D.; Rathgeb, X. Org. Lett. 2007, 9, 3393-3395
23. Polet, D.; Rathgeb, X.; Falciola, C. A.; Langlois, J.-B.; Hajjaji, S. E.; Alexakis, A. Chem.-Eur. J. 2009, 15, 1205-1216
24. Selim, K. B.; Yamada, K.; Tomioka, K. Chem. Commun. 2008, 5140-5142
25. Our studies on chiral NHC: Matsumoto, Y.; Yamada, K.; Tomioka, K. J. Org. Chem. 2008, 73, 4578-4581
26. Matsumoto, Y.; Selim, K. B.; Nakanishi, H.; Yamada, K.; Yamamoto, Y.; Tomioka, K. Tetrahedron Lett. 2010, 51, 404-406
27. Selim, K. B.; Matsumoto, Y.; Yamada, K.; Tomioka, K. Angew. Chem., Int. Ed. 2009, 48, 8733-8735
28. Cu-catalyzed AAA using monodentate NHC and alkyl Grignard reagents: Tominaga, S.; Oi, Y.; Kato, T.; An, D. K.; Okamoto, S. Tetrahedron Lett. 2004, 45, 5585-5588 See also ref 6c: bidentate NHC and dialkylzincs. Larsen, A. O.; Leu, W.; Oberhuber, C. N.; Campbell, J. E.; Hoveyda, A. H. J. Am. Chem. Soc. 2004, 126, 11130-11131
29. Van Veldhuizen, J. J.; Campbell, J. E.; Giudici, R. E.; Hoveyda, A. H. J. Am. Chem. Soc. 2005, 127, 6877-6882
30. Bidentate NHC and vinylaluminums; see ref 9.
31. Cu-catalyzed AAAr of vinylsilane substrates using bidentate NHC and diarylzincs, see ref 7.
32. Cu-free AAA using an NHC and alkyl Grignard reagents: Jackowski, O.; Alexakis, A. Angew. Chem., Int. Ed. 2010, 49, 3346-3350
33. Leading references: Goering, H. L.; Singleton, V. D., Jr. J. Am. Chem. Soc. 1976, 98, 7854-7855
34. Levisalles, J.; Rudler-Chauvin, M.; Rudler, H. J. Orgonomet. Chem. 1977, 136, 103-110
35. Magid, R. M. Tetrahedron 1980, 36, 1901-1930
36. Goering, H. L.; Singleton, V. D., Jr. J. Org. Chem. 1983, 48, 1531-1533
37. Goering, H. L.; Kantner, S. S. J. Org. Chem. 1984, 49, 422-426
38. Corey, E. J.; Boaz, N. W. Tetrahedron Lett. 1984, 25, 3063-3066
39. Keinan, E.; Bosch, E. J. Org. Chem. 1986, 51, 4006-4016
40. Bäckvall, J. E.; Sellen, M.; Grant, B. J. Am. Chem. Soc. 1990, 112, 6615-6621
41. Goering, H. L.; Underiner, T. L. J. Org. Chem. 1991, 56, 2563-2672
42. Bäckvall, J. E.; Persson, E. S. M.; Bombrun, A. J. Org. Chem. 1994, 59, 4126-4130
43. Persson, E. S. M.; van Klaveren, M.; Grove, D. M.; Bäckvall, J. E.; van Koten, G. Chem.-Eur. J. 1995, 1, 351-359
44. Yamamoto, T.; Yamamoto, A.; Ikeda, S. J. Am. Chem. Soc. 1971, 93, 3350-3360
45. Kurosawa, H.; Emoto, M.; Ohnishi, H.; Miki, K.; Tatsumi, K.; Nakamura, A. J. Am. Chem. Soc. 1987, 109, 6333-6340
46. Collman, J. P.; Hegedus, L. S.; Norton, J. R.; Finke, R. G.; Principles and Applications of Organotransition Metal Chemistry; University Science Books: Mill Valley, CA, 1987.
47. Evaluation of the NHCs using the in situ -generated NHC-CuTC can be justified because the reaction with the in situ -generated CuTC analogues of 1a and 1b gave almost the same results (97% yield, 88% ee, γ/α 67:33 and 82% yield, 77% ee, γ/α 90:10, respectively) as those of 1a and 1b shown in Table 1, entries 1 and 2.
48. Allred, G. D.; Liebeskind, L. S. J. Am. Chem. Soc. 1996, 118, 2748-2749
49. Tallman, K. A.; Roschek, B., Jr.; Porter, N. A. J. Am. Chem. Soc. 2004, 126, 9240-9247
50. Tallman, K. A.; Rector, C. L.; Porter, N. A. J. Am. Chem. Soc. 2009, 131, 5635-5641
51. Mixer, R. Y.; Young, W. G. J. Am. Chem. Soc. 1956, 78, 3379-3384
52. Dübner, F.; Knochel, P. Tetrahedron Lett. 2000, 41, 9233-9237
53. Miyaura, N.; Itoh, M.; Suzuki, A. Bull. Chem. Soc. Jpn. 1977, 50, 2199-2200
54. Lardicci, L.; Menicagli, R. J. Org. Chem. 1972, 37, 1060-1062
55. Caporusso, A. M.; Zampieri, A.; Aronica, L. A.; Banti, D. J. Org. Chem. 2006, 71, 1902-1910
56. Murakata, M.; Tsutsui, H.; Hoshino, O. Org. Lett. 2001, 3, 299-302