Catalytic asymmetric synthesis of nitrocyclopropane carboxylates

Tetrahedron

Volumn 68, Issue 17, 2012, Pages 3487-3496

  Moreau, Benoît ^a   Alberico, Dino ^a   Lindsay, Vincent N G ^a   Charette, André B ^a  

^a UNIVERSITÉ DE MONTRÉAL   (Canada)

Author keywords

Asymmetric catalysis; Bis(oxazolines); Copper; Cyclopropanation; Nitrocyclopropane carboxylates

Indexed keywords

1 NITROCYCLOPROPYL CARBOXYLATE; ALKENE; CARBOXYLIC ACID DERIVATIVE; COPPER; NITROCYCLOPROPANE CARBOXYLATE; UNCLASSIFIED DRUG; ZINC;

ASYMMETRIC CATALYSIS; ASYMMETRIC SYNTHESIS; CATALYTIC ASYMMETRIC SYNTHESIS; CONFERENCE PAPER; CONTROLLED STUDY; CYCLOPROPANATION; ENANTIOSELECTIVITY; ISOMER; PRIORITY JOURNAL; REDUCTION;

EID: 84859556210     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2011.05.113     Document Type: Conference Paper

References (81)

1. R. Ballini, A. Palmieri, and D. Fiorini ARKIVOC vii 2007 172
2. D. Seebach, R. Haener, and T. Vettiger Helv. Chim. Acta 70 1987 1507
3. T. Vettiger, and D. Seebach Liebigs Ann. Chem. 1990 195
4. For an efficient synthesis of all isomers of cyclopropane α-amino acids also through metal carbene intermediates, see: H.M.L. Davies, P.R. Bruzinski, D.H. Lake, N. Kong, and M.J. Fall J. Am. Chem. Soc. 118 1996 6897
5. P.E. O'Bannon, and W.P. Dailey Tetrahedron 46 1990 7341
6. E.M. Budynina, O.A. Ivanova, E.B. Averina, T.S. Kuznetsova, and N.S. Zefirov Tetrahedron Lett. 47 2006 647
7. O. Lifchits, and A.B. Charette Org. Lett. 10 2008 2809
8. O. Lifchits, D. Alberico, I. Zakharian, and A.B. Charette J. Org. Chem. 73 2008 6838
9. R.P. Wurz, and A.B. Charette Org. Lett. 7 2005 2313
10. R.P. Wurz, and A.B. Charette J. Org. Chem. 69 2004 1262
11. N.V. Yashin, E.B. Averina, S.M. Gerdov, T.S. Kuznetsova, and N.S. Zefirov Tetrahedron Lett. 44 2003 8241
12. For reviews on cyclopropane amino acids, see: F. Brackmann, and A. de Meijere Chem. Rev. 107 2007 4493
13. F. Brackmann, and A. de Meijere Chem. Rev. 107 2007 4538
14. R.A. Pages, and A. Burger J. Med. Chem. 9 1966 766
15. R.A. Pages, and A. Burger J. Med. Chem. 10 1967 435
16. E. Muray, J. Rifé, V. Branchadell, and R.M. Ortuño J. Org. Chem. 67 2002 4520
17. A.I. Jiménez, P. López, and C. Cativiela Chirality 17 2004 22
18. L.A. Adams, J.P.H. Charmant, R.J. Cox, M. Walter, and W.G. Whittingham Org. Biomol. Chem. 2 2004 542
19. J.A. Frick, J.B. Klassen, and H. Rapoport Synthesis 2005 1751
20. A.I. Jiménez, R. Vanderesse, M. Marraud, A. Aubry, and C. Cativiela Tetrahedron Lett. 38 1997 7559
21. C. Cativiela, and M.D. Díaz-de-Villegas Tetrahedron: Asymmetry 9 1998 3517
22. A.I. Jiménez, C. Cativiela, A. Aubry, and M. Marraud J. Am. Chem. Soc. 120 1998 9452
23. D. Moye-Sherman, S. Jin, I. Ham, D. Lim, J.M. Scholtz, and K. Burgess J. Am. Chem. Soc. 120 1998 9435
24. A.I. Jiménez, C. Cativiela, and M. Marraud Tetrahedron Lett. 41 2000 5353
25. C. Alemán, A.I. Jiménez, C. Cativiela, J.J. Pérez, and J. Casanovas J. Phys. Chem. B 106 2002 11849
26. J. Casanovas, A.I. Jiménez, C. Cativiela, J.J. Pérez, and C. Alemán J. Org. Chem. 68 2003 7088
27. S.D. Royo, W.M. De Borggraeve, C. Peggion, F. Formaggio, M. Crisma, A.I. Jiménez, C. Cativiela, and C. Toniolo J. Am. Chem. Soc. 127 2005 2036
28. A.I. Jiménez, G. Ballano, and C. Cativiela Angew. Chem., Int. Ed. 44 2005 396
29. J. Casanovas, A.I. Jiménez, C. Cativiela, J.J. Pérez, and C. Alemán J. Phys. Chem. B 110 2006 5762
30. S.F. Yang, and N.E. Hoffmann Annu. Rev. Plant Physiol. 35 1984 155
31. J. Salaün, and M.S. Baird Curr. Med. Chem. 2 1995 511
32. L.F. Burroughs Nature 179 1957 360
33. M.L. Vähätalo, and A.I. Virtanen Acta Chem. Scand. 11 1957 741
34. H. Kakeya, H.-P. Zhang, K. Kobinata, R. Onose, C. Onozawa, T. Kudo, and H. Osada J. Antibiot. 50 1997 370
35. T. Wakamiya, H. Nakamoto, and T. Shiba Tetrahedron Lett. 25 1984 4411
36. A. Ichihara, K. Shiraishi, K. Sakamura, H. Sato, K. Nishiyama, R. Sakai, A. Furusaki, and T. Matsumoto J. Am. Chem. Soc. 99 1977 636
37. S. Ahmad, R.S. Phillips, and C.H. Stammer J. Med. Chem. 35 1992 1410
38. N. Goudreau, D.R. Cameron, P. Bonneau, V. Gorys, C. Plouffe, M. Poirier, D. Lamarre, and M. Llinàs-Brunet J. Med. Chem. 47 2004 123
39. M. Llinàs-Brunet, M.D. Bailey, E. Ghiro, V. Gorys, T. Halmos, M. Poirier, J. Rancourt, and N. Goudreau J. Med. Chem. 47 2004 6584
40. D. Lamarre, P.C. Anderson, M. Bailey, P. Beaulieu, G. Bolger, P. Bonneau, M. Bös, D.R. Cameron, M. Cartier, M.G. Cordingley, A.-M. Faucher, N. Goudreau, S.H. Kawai, G. Kukolj, L. Lagacé, S.R. LaPlante, H. Narjes, M.-A. Poupart, J. Rancourt, R.E. Sentjens, R. St. George, B. Simoneau, G. Steinmann, D. Thibeault, Y.S. Tsantrizos, S.M. Weldon, C.-L. Yong, and M. Llinàs-Brunet Nature 426 2003 186
41. P.L. Beaulieu, J. Gillard, M.D. Bailey, C. Boucher, J.S. Duceppe, B. Simoneau, X.-J. Wang, L. Zhang, K. Grozinger, I. Houpis, V. Farina, H. Heimroth, T. Krueger, and J. Schnaubelt J. Org. Chem. 70 2005 5869
42. P.E. O'Bannon, and W.P. Dailey J. Org. Chem. 54 1989 3096
43. S. Zhu, J.A. Perman, and X.P. Zhang Angew. Chem., Int. Ed. 47 2008 8460
44. V.N.G. Lindsay, W. Lin, and A.B. Charette J. Am. Chem. Soc. 131 2009 16383
45. A.B. Charette, R.P. Wurz, and T. Ollevier Helv. Chim. Acta 85 2002 4468
46. R.P. Wurz, and A.B. Charette Org. Lett. 5 2003 2327
47. B. Moreau, and A.B. Charette J. Am. Chem. Soc. 127 2005 18014
48. A similar counterion effect was reported for a copper(II)-bis(oxazoline) complex, see: D.A. Evans, J.A. Murry, P. von Matt, R.D. Norcross, and S.J. Miller Angew. Chem., Int. Ed. Engl. 34 1995 798
49. A.K. Ghosh, P. Mathivanan, and J. Cappiello Tetrahedron: Asymmetry 9 1998 1
50. H.A. McManus, and P.J. Guiry Chem. Rev. 104 2004 4151
51. G. Desimoni, G. Faita, and A. Jorgensen Chem. Rev. 106 2006 3561
52. E.J. Corey, N. Imai, and H.Y. Zhang J. Am. Chem. Soc. 113 1991 728
53. S.H. Kang, and M. Kim J. Am. Chem. Soc. 125 2003 4684
54. S. Crosignani Tetrahedron 54 1998 15721
55. D.A. Evans, K.A. Woerpel, M.M. Hinman, and M.M. Faul J. Am. Chem. Soc. 113 1991 726
56. I.W. Davies, C.H. Senanayake, R.D. Larsen, T.R. Verhoeven, and P.J. Reider Tetrahedron Lett. 37 1996 1725
57. R.E. Lowenthal, A. Abiko, and S. Masamune Tetrahedron Lett. 31 1990 6005
58. M.P. Sibi, and J.G. Ji J. Org. Chem. 62 1997 3800
59. A.B. Charette, M.K. Janes, and H. Lebel Tetrahedron: Asymmetry 14 2003 867
60. E.J. Corey, and K. Ishihara Tetrahedron Lett. 33 1992 6807
61. M. Itagaki, K. Masumoto, and Y. Yamamoto J. Org. Chem. 70 2005 3292
62. For the Lewis acid promoted racemization of similar substrates, see: P.D. Pohlhaus, and J.S. Johnson J. Am. Chem. Soc. 127 2005 16014 Difficulties isolating this product compared to other substrates and the formation of large amounts of cyclopropane ring-opening product support this hypothesis
63. E.N. Jacobsen, A. Pfaltz, and H. Yamamoto Comprehensive Asymmetric Catalysis Vol. 2 1999 Springer Berlin 513 538
64. J.M. Fraile, J.I. García, V. Martínez-Merino, J.A. Mayoral, and L. Salvatella J. Am. Chem. Soc. 123 2001 7616
65. T. Rasmussen, J.F. Jensen, N. Østergaard, D. Tanner, T. Ziegler, and P.-O. Norrby Chem. - Eur. J. 8 2002 177
66. D. Marcoux, and A.B. Charette Angew. Chem., Int. Ed. 47 2008 10155
67. D. Marcoux, S.R. Goudreau, and A.B. Charette J. Org. Chem. 74 2009 8939
68. M.P. Doyle, M.A. McKervey, and T. Ye Modern Catalytic Methods for Organic Synthesis with Diazo Compounds: From Cyclopropanes to Ylides 1998 Wiley New York, NY 169 180
69. M.P. Doyle, R.L. Dorow, W.E. Buhro, J.H. Griffin, W.H. Tamblyn, and M.L. Trudell Organometallics 3 1984 44
70. M.P. Doyle, J.H. Griffin, V. Bagheri, and R.L. Dorow Organometallics 3 1984 53
71. P.A. Wade, P.A. Kondracki, and P.J. Carroll J. Am. Chem. Soc. 113 1991 8807
72. P.E. O'Bannon, and W.P. Dailey J. Am. Chem. Soc. 111 1989 9244
73. B.D. Zlatopolskiy, K. Loscha, P. Alvermann, S.I. Kozhushkov, S.V. Nikolaev, A. Zeeck, and A. de Meijere Chem. - Eur. J. 10 2004 4708
74. It has been reported that the deprotonation/functionalization of nitrocyclopropane with various bases and electrophiles resulted in only dimerized products and no desired functionalized product: Y. Kai, P. Knochel, S. Kwaitkowski, J.D. Dunitz, J.F.M. Oth, D. Seebach, and H.-O. Kalinowski Helv. Chim. Acta 65 1982 137
75. P.E. O'Bannon, and W.P. Dailey J. Org. Chem. 55 1990 353
76. R.M. Moriarty, B.R. Bailey III, O. Prakash, and I. Prakash J. Am. Chem. Soc. 107 1985 1375
77. A.B. Charette, and R.P. Wurz J. Mol. Catal. A 196 2003 83
78. R. Csuk, M.J. Schabel, and Y. von Scholtz Tetrahedron: Asymmetry 7 1996 3505
79. I. Arenal, M. Bernabé, E. Fernandez-Alvarez, and S. Penadéz Synthesis 1985 773
80. C. Cativiela, M.D. Díaz de Villegas, J.A. Mayoral, and E. Meléndez J. Org. Chem. 50 1985 3167
81. A. Bondon, T.L. Macdonald, T.M. Harris, and F.P. Guengerich J. Biol. Chem. 264 1989 1988