Direct catalytic enantio- and diastereoselective ketone aldol reactions of isocyanoacetates

Angewandte Chemie - International Edition

Volumn 54, Issue 16, 2015, Pages 4895-4898

  De La Campa, Raquel ^a   Ortín, Irene ^a   Dixon, Darren J ^a  

^a UNIVERSITY OF OXFORD   (United Kingdom)

Author keywords

aldol reaction; asymmetric catalysis; enantioselectivity; isocyanoacetates; oxazolines

Indexed keywords

CHEMICAL REACTIONS; CONDENSATION REACTIONS; ENANTIOSELECTIVITY; NITROGEN COMPOUNDS; SILVER OXIDES; STEREOSELECTIVITY;

ALDOL REACTIONS; ASYMMETRIC CATALYSIS; BINARY CATALYST SYSTEMS; CHIRAL OXAZOLINES; DIASTEREOSELECTIVE; DIASTEREOSELECTIVITIES; ISOCYANOACETATES; OXAZOLINES;

KETONES;

EID: 84926467643     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201411852     Document Type: Article

References (62)

1. R. Mahrwald, in Modern Aldol Reactions, Wiley-VCH, Weinheim, 2004
2. B. M. Trost, C. S. Brindle, Chem. Soc. Rev. 2010, 39, 1600-1632
3. C. Palomo, M. Oiarbide, J. M. García, Chem. Soc. Rev. 2004, 33, 65-75
4. L. M. Geary, P. G. Hultin, Tetrahedron: Asymmetry 2009, 20, 131-173.
5. K. C. Nicolaou, C. N. C. Boddy, S. Bräse, N. Winssinger, Angew. Chem. Int. Ed. 1999, 38, 2096-2152
6. Angew. Chem. 1999, 111, 2230-2287
7. M. K. Renner, Y. Shen, X. Cheng, P. R. Jensen, W. Frankmoelle, C. A. Kauffman, W. Fenical, E. Lobkovsky, J. Clardy, J. Am. Chem. Soc. 1999, 121, 11273-11276
8. B. Herbert, I. H. Kim, K. L. Kirk, J. Org. Chem. 2001, 66, 4892-4897.
9. J. P. Guthrie, J. Am. Chem. Soc. 1991, 113, 7249-7255
10. M. Hatano, E. Takagi, K. Ishihara, Org. Lett. 2007, 9, 4527-4530.
11. S. E. Denmark, Y. Fan, J. Am. Chem. Soc. 2002, 124, 4233-4235
12. S. E. Denmark, Y. Fan, M. D. Eastgate, J. Org. Chem. 2005, 70, 5235-5248; for reactions with enol silanes, see
13. K. Oisaki, D. Zhao, M. Kanai, M. Shibasaki, J. Am. Chem. Soc. 2006, 128, 7164-7165
14. K. Oisaki, Y. Suto, M. Kanai, M. Shibasaki, J. Am. Chem. Soc. 2003, 125, 5644-5645
15. X. Moreau, B. Bazan-Tejada, J. Campagne, J. Am. Chem. Soc. 2005, 127, 7288-7289; for reductive aldol reactions, see
16. H. W. Laim, P. M. Joensuu, Org. Lett. 2005, 7, 4225-4228
17. J. Deschamp, O. Chuzel, J. Hannedouche, O. Riant, Angew. Chem. Int. Ed. 2006, 45, 1292-1297
18. Angew. Chem. 2006, 118, 1314-1319; see also
19. S. Adachi, T. Harada, Eur. J. Org. Chem. 2009, 3661-3671.
20. E. J. Corey, A. Guzman-Perez, Angew. Chem. Int. Ed. 1998, 37, 388-401
21. Angew. Chem. 1998, 110, 402-415
22. O. Riant, J. Hannedouche, Org. Biomol. Chem. 2005, 5, 873-888
23. P. G. Cozzi, R. Hilgraf, N. Zimmermann, Eur. J. Org. Chem. 2007, 5969-5994
24. M. Shibasaki, M. Kanai, Chem. Rev. 2008, 108, 2853-2873
25. M. Hatano, K. Ishihara, Synthesis 2008, 1647-1675.
26. A. V. Gulevich, A. G. Zhdanko, R. V. A. Orru, V. G. Nenajdenko, Chem. Rev. 2010, 110, 5235-5331; see also
27. W. A. Böll, F. Gerhart, A. Nürrenbach, U. Schöllkopf, Angew. Chem. Int. Ed. Engl. 1970, 9, 458-459
28. Angew. Chem. 1970, 82, 482-483
29. Y. Ito, T. Matsuura, T. Saegusa, Tetrahedron Lett. 1985, 26, 5781-5784.
30. Y. Ito, M. Sawamura, T. Hayashi, J. Am. Chem. Soc. 1986, 108, 6405-6406
31. Y. Ito, M. Sawamura, T. Hayashi, Tetrahedron Lett. 1987, 28, 6215-6218
32. S. D. Pastor, A. Togni, J. Am. Chem. Soc. 1989, 111, 2333-2334
33. T. Hayashi, Y. Uozumi, A. Yamzaki, M. Sawamura, H. Hamashima, Y. Ito, Tetrahedron Lett. 1991, 32, 2799-2802
34. T. Hayashi, M. Sawamura, Y. Ito, Tetrahedron 1992, 48, 1999-2012
35. V. A. Soloshonok, T. Hayashi, Tetrahedron Lett. 1994, 35, 2713-2716
36. V. A. Soloshonok, A. Kacharov, T. Hayashi, Tetrahedron 1996, 52, 245-254
37. J. M. Longmire, X. Zhang, Organometallics 1998, 17, 4374-4379
38. M. Sawamura, Y. Nakayama, T. Kato, Y. Ito, J. Org. Chem. 1995, 60, 1727-1732
39. S. Gosiewska, M. H. Veld, J. J. M. de Pater, P. C. A. Bruijnincx, M. Lutz, A. L. Spek, G. van Koten, R. J. M. K. Gebbink, Tetrahedron: Asymmetry 2006, 17, 674-686
40. M. Xue, C. Guo, L. Gong, Synlett 2009, 2191-2197
41. H. Y. Kim, K. Oh, Org. Lett. 2011, 13, 1306-1309
42. F. Sladojevich, A. Trabocchi, A. Guarna, D. J. Dixon, J. Am. Chem. Soc. 2011, 133, 1710-1713.
43. X. Zhou, Y. Lin, L. Dai, J. Sun, L. Xia, M. Tang, J. Org. Chem. 1999, 64, 1331-1334
44. X. Zhou, Y. Lin, L. Dai, Tetrahedron: Asymmetry 1999, 10, 855-862
45. J. Aydin, A. Ryden, K. J. Szabõ, Tetrahedron: Asymmetry 2008, 19, 1867-1870
46. Z. Zhang, G. Lu, M. Chen, N. Lin, Y. Li, T. Hayashi, A. S. C. Chan, Tetrahedron: Asymmetry 2010, 21, 1715-1721
47. P. Shao, J. Liao, Y. A. Ho, Y. Zhao, Angew. Chem. Int. Ed. 2014, 53, 5435-5439
48. Angew. Chem. 2014, 126, 5539-5543.
49. I. Ortín, D. J. Dixon, Angew. Chem. Int. Ed. 2014, 53, 3462-3465
50. Angew. Chem. 2014, 126, 3530-3533
51. M. Hayashi, M. Iwanaga, N. Shiomi, D. Nakane, H. Masuda, S. Nakamura, Angew. Chem. Int. Ed. 2014, 53, 8411-8415
52. Angew. Chem. 2014, 126, 8551-8555.
53. V. A. Soloshonok, A. D. Kacharov, D. V. Avilov, T. Hayashi, Tetrahedron Lett. 1996, 37, 7845-7848
54. V. A. Soloshonok, A. D. Kacharov, D. V. Avilov, K. Ishikawa, N. Nagashima, T. Hayashi, J. Org. Chem. 1997, 62, 3470-3479.
55. T. Yoshino, H. Morimoto, G. Lu, S. Matsunaga, M. Shibasaki, J. Am. Chem. Soc. 2009, 131, 17082-17083
56. S. Matsunaga, T. Yoshino, Chem. Rec. 2011, 11, 260-268.
57. D. Hoppe, U. Schöllkopf, Angew. Chem. Int. Ed. Engl. 1972, 11, 432-433
58. Angew. Chem. 1972, 84, 435-436.
59. CCDC 1036558 (8) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.
60. W. Zeng, G. Chen, Y. Zhou, Y. Li, J. Am. Chem. Soc. 2007, 129, 750-751
61. G. Liang, M. Tong, C. Wang, Adv. Synth. Catal. 2009, 351, 3101-3106
62. J. Song, C. Guo, P. Chen, J. Yu, S. Luo, L. Gong, Chem. Eur. J. 2011, 17, 7786-7790.