Catalytic asymmetric Payne oxidation under the catalysis of P-spiro chiral triaminoiminophosphorane: Application to the synthesis of N-sulfonyl oxaziridines

Tetrahedron

Volumn 70, Issue 8, 2014, Pages 1691-1701

  Uraguchi, Daisuke ^a   Tsutsumi, Ryosuke ^a   Ooi, Takashi ^a,b  

^a NAGOYA UNIVERSITY   (Japan)

^b JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

Author keywords

Asymmetric catalysis; Hydrogen peroxide; Imine; Organocatalysis; Oxaziridine

Indexed keywords

EID: 84895066521     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2013.12.086     Document Type: Article

References (68)

1. S.-O. Lawesson, and G. Schroll S. Patai, The Chemistry of Carboxylic Acids and Esters 1969 John Wiley New York, NY 669 703 Chapter 14
2. L. Shu, and Y. Shi Tetrahedron Lett. 40 1999 8721
3. L. Shu, and Y. Shi Tetrahedron 57 2001 5213
4. Z.-X. Wang, L. Shu, M. Frohn, Y. Tu, and Y. Shi Org. Synth. 80 2003 9
5. G. Peris, C.E. Jakobsche, and S.J. Miller J. Am. Chem. Soc. 129 2007 8710
6. C.E. Jakobsche, G. Peris, and S.J. Miller Angew. Chem., Int. Ed. 47 2008 6707
7. G. Peris, and S.J. Miller Org. Lett. 10 2008 3049
8. F. Kolundzic, M.N. Noshi, M. Tjandra, M. Movassaghi, and S.J. Miller J. Am. Chem. Soc. 133 2011 9104
9. G.B. Payne, P.H. Deming, and P.H. Williams J. Org. Chem. 26 1961 659
10. G.B. Payne Tetrahedron 18 1962 763
11. R.D. Bach, and J.W. Knight Org. Synth. 60 1981 63
12. L.A. Arias, S. Adkins, C.J. Nagel, and R.D. Bach J. Org. Chem. 48 1983 888
13. T. Werner Adv. Synth. Catal. 351 2009 1469
14. D. Enders, and T.V. Nguyen Org. Biomol. Chem. 10 2012 5327
15. For a review on organic base catalysis, see: C. Palomo, M. Oiarbide, and R. López Chem. Soc. Rev. 38 2009 632
16. R. Schwesinger, and H. Schlemper Angew. Chem., Int. Ed. Engl. 26 1987 1167 For review, see
17. T. Ishikawa Superbases for Organic Synthesis: Guanidines, Amidines, Phosphazenes and Related Organocatalysts 2009 John Wiley West Sussex, U.K.
18. D. Uraguchi, and T. Ooi J. Synth. Org. Chem. Jpn. 68 2010 1185
19. D. Uraguchi, S. Nakamura, and T. Ooi Angew. Chem., Int. Ed. 49 2010 7562
20. D. Uraguchi, Y. Ueki, and T. Ooi Angew. Chem., Int. Ed. 50 2011 3681
21. D. Uraguchi, Y. Ueki, and T. Ooi Chem. Sci. 3 2012 842
22. M.T. Corbett, D. Uraguchi, T. Ooi, and J.S. Johnson Angew. Chem., Int. Ed. 51 2012 4685
23. D. Uraguchi, K. Yoshioka, Y. Ueki, and T. Ooi J. Am. Chem. Soc. 134 2012 19370
24. D. Uraguchi, Y. Ueki, A. Sugiyama, and T. Ooi Chem. Sci. 4 2013 1308
25. D. Uraguchi, R. Tsutsumi, and T. Ooi J. Am. Chem. Soc. 135 2013 8161
26. W.D. Emmons J. Am. Chem. Soc. 78 1956 6208
27. D.R. Boyd, J.F. Malone, M.R. McGuckin, W.B. Jennings, M. Rutherford, and B.M. Saket J. Chem. Soc., Perkin Trans. 2 1988 1145
28. L. Martiny, and K.A. Jørgensen J. Chem. Soc., Perkin Trans. 1 1995 699
29. J.A. Damavandi, B. Karami, and M.A. Zolfigol Synlett 2002 933
30. J.-P. Schirmann, and F. Weiss Tetrahedron Lett. 13 1972 633
31. J. KräIem, Y. Kacem, J. Khiari, and B. Ben Hassine Synth. Commun. 31 2001 263
32. J. KräIem, R. Ben Othman, and B. Ben Hassine C. R. Chim. 7 2004 1119
33. N. Tka, J. KräIem, and B. Ben Hassine Synth. Commun. 42 2012 2994
34. L. Lykke, C. Rodríguez-Escrich, and K.A. Jørgensen J. Am. Chem. Soc. 133 2011 14932
35. J.L. Olivares-Romero, Z. Li, and H. Yamamoto J. Am. Chem. Soc. 134 2012 5440
36. S. Dong, X. Liu, Y. Zhu, P. He, L. Lin, and X. Feng J. Am. Chem. Soc. 135 2013 10026
37. For review on asymmetric hydroxylation of enolates with N-sulfonyloxaziridines, see: F.A. Davis, and B.-C. Chen Chem. Rev. 92 1992 919
38. F.A. Davis, U.K. Nadir, and E.W. Kluger J. Chem. Soc., Chem. Commun. 1977 25
39. F.A. Davis, R. Jenkins Jr., and S.G. Yocklovich Tetrahedron Lett. 19 1978 5171
40. F.A. Davis, M.E. Harakal, and S.B. Awad J. Am. Chem. Soc. 105 1983 3123
41. F.A. Davis, J.M. Billmers, D.J. Gosciniak, J.C. Towson, and R.D. Bach J. Org. Chem. 51 1986 4240
42. F.A. Davis, and A.C. Sheppard Tetrahedron 45 1989 5703
43. V.A. Petrov, and G. Resnati Chem. Rev. 96 1996 1809
44. S. Andreae, and E. Schmitz Synthesis 1991 327
45. D.R. Anderson, K.W. Woods, and P. Beak Org. Lett. 1 1999 1415
46. B.H. Brodsky, and J. Du Bois J. Am. Chem. Soc. 127 2005 15391
47. R. Ramage, J. Green, and A.J. Blake Tetrahedron 47 1991 6353
48. T. Ooi, Y. Uematsu, J. Fujimoto, K. Fukumoto, and K. Maruoka Tetrahedron Lett. 48 2007 1337
49. I. Saito, R. Nagata, K. Yuba, and T. Matsuura Tetrahedron Lett. 24 1983 1737
50. N. Sasakura, K. Nakano, Y. Ichikawa, and H. Kotsuki RSC Adv. 2 2012 6135
51. For review on aminohydroxylation of olefins using oxaziridines, see: C.E.I. Knappke, and A.J. von Wangelin ChemCatChem 2 2010 1381
52. D.J. Michaelis, C.J. Shaffer, and T.P. Yoon J. Am. Chem. Soc. 129 2007 1866
53. K.M. Partridge, M.E. Anzovino, and T.P. Yoon J. Am. Chem. Soc. 130 2008 2920
54. D.J. Michaelis, M.A. Ischay, and T.P. Yoon J. Am. Chem. Soc. 130 2008 6610
55. D.J. Michaelis, K.S. Williamson, and T.P. Yoon Tetrahedron 65 2009 5118
56. T. Benkovics, J. Du, I.A. Guzei, and T.P. Yoon J. Org. Chem. 74 2009 5545
57. C.P. Allen, T. Benkovics, A.K. Turek, and T.P. Yoon J. Am. Chem. Soc. 131 2009 12560
58. K.M. Partridge, I.A. Guzei, and T.P. Yoon Angew. Chem., Int. Ed. 49 2010 930
59. K.S. Williamson, and T.P. Yoon J. Am. Chem. Soc. 132 2010 4570
60. S.M. DePorter, A.C. Jacobsen, K.M. Partridge, K.S. Williamson, and T.P. Yoon Tetrahedron Lett. 51 2010 5223
61. T. Benkovics, I.A. Guzei, and T.P. Yoon Angew. Chem., Int. Ed. 49 2010 9153
62. K.S. Williamson, and T.P. Yoon J. Am. Chem. Soc. 134 2012 12370
63. J. KräIem, L. Grosvalet, M. Perrin, and B. Ben Hassine Tetrahedron Lett. 42 2001 9131
64. M. Fabio, L. Ronzini, and L. Troisi Tetrahedron 63 2007 12896
65. H.F. Motiwala, B. Gülgeze, and J. Aubé J. Org. Chem. 77 2012 7005
66. N. Richy, M. Ghoraf, and J. Vidal J. Org. Chem. 77 2012 10972
67. K. Lu, and O. Kwon Org. Synth. 86 2009 212
68. F. Chemla, V. Hebbe, and J.-F. Normant Synthesis 2000 75