Chiral zinc-catalyzed asymmetric α-alkylallylation and α-chloroallylation of aldehydes

Angewandte Chemie - International Edition

Volumn 50, Issue 51, 2011, Pages 12262-12265

  Kobayashi, Shå ^a   Endo, Toshimitsu ^a   Ueno, Masaharu ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

addition; aldehydes; allylation; asymmetric catalysis; synthetic methods

Indexed keywords

ALLYLBORONATES; ASYMMETRIC CATALYSIS; BIPYRIDINE LIGANDS; DIASTEREO- AND ENANTIOSELECTIVITY; HIGH YIELD; HOMOALLYLIC ALCOHOL; STEREOGENIC CENTERS; SYNTHETIC METHODS;

ALLYLATION; CATALYSIS; ORGANIC COMPOUNDS; ZINC;

ALDEHYDES;

EID: 83755196032     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201106433     Document Type: Article

References (89)

1. Catalytic Asymmetric Synthesis (Ed.:, I. Ojima,), Wiley, New York, 2010.
2. H. Lachance, D. G. Hall, Org. React. 2008, 73, 1
3. S. E. Denmark, J. Fu, Chem. Rev. 2003, 103, 2763
4. S. E. Denmark, N. G. Almstead, in Modern Carbonyl Chemistry (Ed.:, J. Otera,), Wiley-VCH, Weinheim, 2000, chap. 10, pp. 299-402
5. S. R. Chemler, W. R. Roush, in Modern Carbonyl Chemistry (Ed.:, J. Otera,), Wiley-VCH, Weinheim, 2000, chap. 11, pp. 403-490.
6. A. L. Costa, M. G. Piazza, E. Tagliavini, C. Trombini, A. Umani-Rochi, J. Am. Chem. Soc. 1993, 115, 7001
7. G. E. Keck, K. H. Tarbet, L. S. Geraci, J. Am. Chem. Soc. 1993, 115, 8467
8. A. Yanagisawa, H. Nakashima, A. Ishiba, H. Yamamoto, J. Am. Chem. Soc. 1996, 118, 4723.
9. K. Furuta, M. Mouri, H. Yamamoto, Synlett 1991, 561
10. K. Ishihara, M. Mouri, Q. Z. Gao, T. Maruyama, K. Furuta, H. Yamamoto, J. Am. Chem. Soc. 1993, 115, 11490
11. D. R. Gauthier, E. M. Carreira, Angew. Chem. 1996, 108, 2521
12. Angew. Chem. Int. Ed. Engl. 1996, 35, 2363
13. M. Wadamoto, N. Ozasa, A. Yanagisawa, H. Yamamoto, J. Org. Chem. 2003, 68, 5593
14. S. E. Denmark, J. Fu, J. Am. Chem. Soc. 2001, 123, 9488
15. S. E. Denmark, J. Fu, Chem. Commun. 2003, 167
16. A. V. Malkov, L. Dufkova, L. Farrugia, P. Kocovsky, Angew. Chem. 2003, 115, 3802
17. Angew. Chem. Int. Ed. 2003, 42, 3674
18. A. V. Malkov, M. Bell, F. Castelluzzo, P. Kocovsky, Org. Lett. 2005, 7, 3219.
19. For other representative catalytic asymmetric allylations of aldehydes, see
20. C. Chen, K. Tagami, Y. Kishi, J. Org. Chem. 1995, 60, 5386
21. A. Fürstner, N. Shi, J. Am. Chem. Soc. 1996, 118, 12349
22. M. Bandini, P. G. Cozzi, P. Melchiorre, A. Umani-Rochi, Angew. Chem. 1999, 111, 3558
23. Angew. Chem. Int. Ed. 1999, 38, 3357
24. H. W. Choi, K. Nakajima, D. Demeke, F. A. Kang, H. S. Jun, Z. K. Wan, Y. Kishi, Org. Lett. 2002, 4, 4431
25. A. Fürstner, M. Wuchrer, Chem. Eur. J. 2006, 12, 76
26. G. Xia, H. Yamamoto, J. Am. Chem. Soc. 2006, 128, 2554
27. I. S. Kim, M.-Y. Ngai, M. J. Krische, J. Am. Chem. Soc. 2008, 130, 14891
28. I. S. Kim, S. B. Han, M. J. Krische, J. Am. Chem. Soc. 2008, 130, 6340.
29. J. W. J. Kennedy, D. G. Hall, J. Am. Chem. Soc. 2002, 124, 11586
30. T. Ishiyama, T.-A. Ahiko, N. Miyaura, J. Am. Chem. Soc. 2002, 124, 12414
31. V. Rauniyar, D. G. Hall, J. Am. Chem. Soc. 2004, 126, 4518
32. S. H. Yu, M. J. Ferguson, R. McDonald, D. G. Hall, J. Am. Chem. Soc. 2005, 127, 12808
33. V. Rauniyar, D. G. Hall, Angew. Chem. 2006, 118, 2486
34. Angew. Chem. Int. Ed. 2006, 45, 2426
35. D. G. Hall, Synlett 2007, 1644
36. V. Rauniyar, H. Zhai, D. G. Hall, J. Am. Chem. Soc. 2008, 130, 8481
37. V. Rauniyar, D. G. Hall, J. Org. Chem. 2009, 74, 4236
38. P. Jain, J. C. Antilla, J. Am. Chem. Soc. 2010, 132, 11884
39. R. Wada, K. Oisaki, M. Kanai, M. Shibasaki, J. Am. Chem. Soc. 2004, 126, 8910
40. S. Lou, P. N. Moquist, S. E. Schaus, J. Am. Chem. Soc. 2006, 128, 12660
41. D. S. Barnett, P. N. Moquist, S. E. Schaus, Angew. Chem. 2009, 121, 8835
42. Angew. Chem. Int. Ed. 2009, 48, 8679
43. P. Zhang, J. P. Morken, J. Am. Chem. Soc. 2009, 131, 12550.
44. Numerous studies have been done in the area of carbonyl allylboration, including asymmetric reactions with chiral boron reagents (using stoichiometric amounts of chiral sources). For selected papers, see
45. R. W. Hoffmann, Pure Appl. Chem. 1990, 62, 1993
46. R. W. Hoffmann, Pure Appl. Chem. 1988, 60, 123
47. H. C. Brown, U. S. Racherla, P. J. Pellechia, J. Org. Chem. 1990, 55, 1868
48. P. V. Ramachandran, Aldrichimica Acta 2002, 35, 23. See also Ref. [6f] and references cited therein. More recently, Ir-catalyzed, enantioselective carbonyl allylation using allyl acetates as allyl metal surrogates has been reported. Selected papers
49. I. S. Kim, S. B. Han, M. J. Krische, J. Am. Chem. Soc. 2009, 131, 2514
50. S. B. Han, X. Gao, J. Krische, J. Am. Chem. Soc. 2010, 132, 9153, and references therein.
51. S. Kobayashi, T. Endo, U. Schneider, M. Ueno, Chem. Commun. 2010, 46, 1260; Cf
52. M. Fujita, T. Nagano, U. Schneider, T. Hamada, C. Ogawa, S. Kobayashi, J. Am. Chem. Soc. 2008, 130, 2914.
53. C. Bolm, M. Zehnder, D. Bur, Angew. Chem. 1990, 102, 206
54. Angew. Chem. Int. Ed. Engl. 1990, 29, 205
55. C. Bolm, M. Ewald, M. Felder, G. Schlingloff, Chem. Ber. 1992, 125, 1169
56. S. Ishikawa, T. Hamada, K. Manabe, S. Kobayashi, Synthesis 2005, 2176.
57. S. Hu, S. Jayaraman, A. C. Oehlschlager, J. Org. Chem. 1999, 64, 3719.
58. I. Paterson, E. A. Anderson, S. M. Dalby, O. Loiseleur, Org. Lett. 2005, 7, 4121
59. A. Fürstner, M. D. B. Fenster, B. Fasching, C. Godbout, K. Radkowski, Angew. Chem. 2006, 118, 5636
60. Angew. Chem. Int. Ed. 2006, 45, 5510
61. I. Paterson, E. A. Anderson, S. M. Dalby, J. H. Lim, O. Loiseleur, P. Maltas, C. Moessner, Pure Appl. Chem. 2007, 79, 667.
62. Although direct observation of the allylzinc species with chiral ligand 4 has not yet been successful, we could detect some allylzinc species with dmp by ESI mass spectrometry.
63. We used methyl pyruvate instead of an aldehyde in the initial kinetic studies, because the reactions with aldehydes were too fast to conduct simple kinetic experiments. While we have already confirmed similarity between aldehydes and methyl pyruvate in this Zn-catalyzed allylation, further kinetic studies using aldehydes are in progress.
64. CCDC 827315 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via.
65. H.-L. Kwong, K.-M. Lau, W.-S. Lee, W.-T. Wong, New J. Chem. 1999, 23, 629.
66. 3+- 4 complex
67. S. Ishikawa, T. Hamada, K. Manabe, S. Kobayashi, J. Am. Chem. Soc. 2004, 126, 12236
68. M. Kokubo, T. Naito, S. Kobayashi, Chem. Lett. 2009, 38, 904.
69. S. J. Archibald, in Comprehensive Coordination Chemistry II, Vol. 6 (Ed.:, D. E. Fenton,), Elsevier, London, 2004, chap. 6.8, pp. 1147-1251.
70. M. Kokubo, T. Naito, S. Kobayashi, Tetrahedron 2010, 66, 1111.
71. Examples of catalytic, highly enantioselective allylation of aldehydes in aqueous media are very rare. See, S. Kobayashi, N. Aoyama, K. Manabe, Chirality 2003, 15, 124, and references therein.
72. T. Krämer, J.-R. Schwark, D. Hoppe, Tetrahedron Lett. 1989, 30, 7037
73. J. A. Marshall, K. W. Hinkle, J. Org. Chem. 1995, 60, 1920
74. D. J. Hallett, E. J. Thomas, Tetrahedron: Asymmetry 1995, 6, 2575
75. G. W. Bradley, D. J. Hallett, E. J Thomas, Tetrahedron: Asymmetry 1995, 6, 2579
76. A. Yanagisawa, S. Habaue, H. Yamamoto, J. Am. Chem. Soc. 1991, 113, 8955
77. A. Yanagisawa, S. Habaue, K. Yasue, H. Yamamoto, J. Am. Chem. Soc. 1994, 116, 6130
78. Y. Yamamoto, K. Maruyama, J. Org. Chem. 1983, 48, 1564
79. H. Miyabe, Y. Yamaoka, T. Naito, Y. Takemoto, J. Org. Chem. 2003, 68, 6745.
80. H. Ito, S. Ito, Y. Sasaki, K. Matsuura, M. Sawamura, J. Am. Chem. Soc. 2007, 129, 14856
81. A. Guzman-Martinez, A. H. Hoveyda, J. Am. Chem. Soc. 2010, 132, 10634
82. X. Gao, D. G. Hall, J. Am. Chem. Soc. 2003, 125, 9308
83. N. F. Pelz, A. R. Woodward, H. E. Burks, J. D. Sieber, J. P. Morken, J. Am. Chem. Soc. 2004, 126, 16328
84. M. Gerdin, C. Moberg, Adv. Synth. Catal. 2005, 347, 749
85. L. Carosi, D. G. Hall, Angew. Chem. 2007, 119, 6017
86. Angew. Chem. Int. Ed. 2007, 46, 5913
87. F. Peng, D. G. Hall, Tetrahedron Lett. 2007, 48, 3305; See also
88. G. Y. Fang, V. K. Aggarwal, Angew. Chem. 2007, 119, 363
89. Angew. Chem. Int. Ed. 2007, 46, 359, and references therein.