A new type of oxidation-reduction condensation by the combined use of phenyl diphenylphosphinite and oxidant

Heterocycles

Volumn 80, Issue 1, 2010, Pages 63-82

  Mukaiyama, Teruaki ^a   Kuroda, Kiichi ^b   Maruyama, Yuji ^b  

^a Tokyo Chemical Industry Company Ltd   (Japan)

^b TOKYO UNIVERSITY OF SCIENCE   (Japan)

Author keywords

Azidation; Esterification; Oxidation Reduction Condensation; Stereoinversion of Chiral Alcohol; Thioetherification

Indexed keywords

EID: 76949085710     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/REV-09-SR(S)1     Document Type: Review

References (80)

1. Mukaiyama T., Kuwajima I., and Suzuki Z. J. Org. Chem. 28 (1963) 2024
2. Mukaiyama T., Mutsueda R., and Suzuki M. Tetrahedron Lett. 11 (1970) 1901
3. Corey E.J., and Nicolaou K.C. J. Am. Chem. Soc. 96 (1974) 5614
4. Corey E.J., Nicolaou K.C., and Melvin L.S. J. Am. Chem. Soc. 97 (1975) 654
5. Corey E.J., Nicolaou K.C., and Melvin L.S. J. Am. Chem. Soc. 97 (1975) 2287
6. Corey E.J., and Bhattacharyya S. Tetrahedron Lett 18 (1977) 3919
7. Mitsunobu O., Yamada M., and Mukaiyama T. Bull. Chem. Soc. Jpn. 40 (1967) 935
8. Mitsunobu O., and Yamada M. Bull. Chem. Soc. Jpn. 40 (1967) 2380
9. For reviews of the Miusunobu reaction, see;. Mitsunobu O. Synthesis (1981) 1
10. Hughes D.L. Org. React. 42 (1992) 335
11. Dembinski R. Eur. J. Org. Chem. (2004) 2763
12. Dandapani S., and Curran D.P. Chem. Eur. J. 10 (2004) 3130
13. But T.Y.S., and Toy P.H. Chem. Asian J. 2 (2007) 1340
14. Tsunoda T., Nagaku M., Nagino C., Kawamura Y., Ozaki F., Hioki H., and Ito S. Tetrahedron Lett. 36 (1995) 2531
15. N2 displacement at quaternary center with various nucleophiles, see:. Shi Y.-J., Hughes D.L., and McNamara J.M. Tetrahedron Lett. 44 (2003) 3609
16. Avenoza A., Busto J.H., Corzana F., Jiménez-Osés G., and Peregrina J.M. Chem. Commun. (2003) 980
17. Kitazume T., Sato T., Kobayashi T., and Lin J.T. J. Org. Chem. 51 (1986) 1003
18. Smith N.D., and Goodman M. Org. Lett. 5 (2003) 1035
19. Effenberger F., and Gaupp S. Tetrahedron: Asymmetry 10 (1999) 1765
20. Wachtmeister J., Mühlman A., Classon B., and Samuelsson B. Tetrahedron 55 (1999) 10761
21. Taber D.F., He Y., and Xu M. J. Am. Chem. Soc. 126 (2004) 13900
22. Masaki Y., Arasaki H., and Iwata M. Chem. Lett 32 (2003) 4
23. For reviews of oxidation-reduction condensation, see:. Mukaiyama T., and Yamabe H. Chem. Lett. 36 (2007) 2
24. Mukaiyama T., Ikegai K., Aoki H., Pluempanupat W., and Masutani K. Proc. Jpn. Acad., Ser. B. 81 (2005) 103
25. Mukaiyama T. Angew. Chem. Int. Ed. 43 (2004) 5590
26. For carbon-oxygen bond formation reactions, see. Mukaiyama T., Shintou T., and Fukumoto K. J. Am. Chem. Soc. 125 (2003) 10538
27. Shintou T., Fukumoto K., and Mukaiyama T. Bull. Chem. Soc. Jpn. 77 (2004) 1569
28. For cyanation and isocyanation, see:. Masutani K., Minowa T., Hagiwara Y., and Mukaiyama T. Bull. Chem. Soc. Jpn. 79 (2006) 1106
29. Mukaiyama T., Masutani K., and Hagiwara Y. Chem. Lett. 33 (2004) 1192
30. Masutani K., Minowa T., and Mukaiyama T. Chem. Lett. 34 (2005) 1142
31. For carbon-sulfur bond formation reactions, see. Ikegai K., Pluempanupat W., and Mukaiyama T. Bull. Chem. Soc. Jpn. 79 (2006) 780
32. Ikegai K., Pluempanupat W., and Mukaiyama T. Chem. Lett. 34 (2005) 638
33. Mukaiyama T., and Ikegai K. Chem. Lett. 33 (2004) 1522
34. For carbon-nitrogen bond formation reactions, see. Aoki H., and Mukaiyama T. Chem. Lett. 35 (2006) 456
35. Aoki H., Kuroda K., and Mukaiyama T. Chem. Lett. 34 (2005) 1266
36. Mukaiyama T., Kuroda K., and Aoki H. Chem. Lett. 34 (2005) 1644
37. Mukaiyama T., and Aoki H. Chem. Lett. 34 (2005) 142
38. For azidation, see:. Kuroda K., Hayashi Y., and Mukaiyama T. Tetrahedron 63 (2007) 6358
39. Kuroda K., Kaneko Y., Hayashi Y., and Mukaiyama T. Chem. Lett. 35 (2006) 1432
40. Kuroda K., Hayashi Y., and Mukaiyama T. Chem. Lett. 37 (2008) 592
41. Kuroda K., Maruyama Y., Hayashi Y., and Mukaiyama T. Bull. Chem. Soc. Jpn. (2009) 82 in press
42. For a review of organic azides, see;. Bräse S., Gil C., Knepper K., and Zimmermann V. Angew. Chem. Int. Ed 44 (2005) 5188
43. Staudinger H., and Meyer J. Helv. Chim. Acta 2 (1919) 635
44. Gololobov Y.G., and Kasukhin L.F. Tetrahedron 48 (1992) 1353
45. Molina P., and Vilaplana M.J. Synthesis (1994) 1197
46. Fresneda P.M., and Molina P. Synlett (2004) 1
47. Eguchi S. Arkivoc ii (2005) 98
48. Palacios F., Alonso C., Aparicio D., Rubiales G., and de los Santos J.M. Tetrahedron 63 (2007) 523
49. Saxon E., and Bertozzi C.R. Science 287 (2000) 2007
50. Saxon E., Luchansky S.J., Hang H.C., Yu C., Lee S.C., and Bertozzi C.R. J. Am. Chem. Soc. 124 (2002) 14893
51. Köhn M., and Breinbauer R. Angew. Chem. Int. Ed 43 (2004) 5590
52. Torii S., Okumoto H., Fujikawa M., and Rashid M.A. Chem. Express. 7 (1992) 933
53. Kuroda K., Maruyama Y., Hayashi Y., and Mukaiyama T. Chem. Lett. 37 (2008) 836
54. Mukaiyama T., Kuroda K., Maruyama Y., and Hayashi Y. Chem. Lett. 37 (2008) 1072
55. Volante R.P. Tetrahedron Lett. 22 (1981) 3119
56. Corey E.J., and Cimprich K.A. Tetrahedron Lett. 33 (1992) 4099
57. 3-ArSSAr), see. Valentine D.H., and Hillhouse J.H. Synthesis (2003) 317
58. Skarżewski J., Gupta A., Wojaczyńska E., and Siedlecka R. Synlett 11 (2003) 1615
59. Kotsuki H., Matsumoto K., and Nishizawa H. Tetrahedron Lett. 32 (1991) 4155
60. Nakazawa I., Aki K., and Hata T. J. Chem. Soc., Perkin Trans. 1 (1983) 1315
61. Nakagawa I., and Hata T. Tetrahedron Lett 16 (1975) 1409
62. Walker K.A.M. Tetrahedron Lett. 18 (1977) 1409
63. Bordwell F.G., and Hughes D.L. J. Org. Chem. 47 (1982) 3224
64. Hughes D.L., and Reamer R.A. J. Org. Chem. 61 (1996) 2967
65. Dodge J.A., Trujillo J.I., and Presnell M. J. Org. Chem. 59 (1994) 234
66. Nenasheva T.N., and Sal'nikova G.A. Zh. Org. Khim. 15 (1979) 835
67. Courtot-Coupez J., and Le Démézet M. Bull. Soc. Chim. Fr. (1969) 1033
68. When thiobenzoic acid was used, side reactions such as amide bond formation might proceed. See. Zaloom J., Calandra M., and Roberts D.C. J. Org. Chem. 50 (1985) 2601
69. Trost B.M., and Fleming I. Comprehensive Organic Synthesis Vol. VI (1991), Pergamon Press, New York 76
70. Hanessian S. Preparative Carbohydrate Chemistry (1997), Marcel Dekker, New York 90 Chapter 5
71. Loibner H., and Zibral E. Helv. Chem. Acta 59 (1976) 2100
72. Lal B., Pramanik B.N., Manhas M.S., and Bose A.K. Tetrahedron Lett. 23 (1977) 1977
73. Viaud M.C., and Rollin P. Synthesis (1990) 130
74. Thompson A.S., Humphrey G.R., DeMarco A.M., Mathre D.J., and Grabowski E.J.J. J. Org. Chem. 58 (1993) 5886
75. Mizuno M., and Shioiri T. Chem. Commun. (1997) 2165
76. Saito A., Saito K., Tanaka A., and Oritani T. Tetrahedron Lett. 38 (1997) 3955
77. Yu C., Liu B., and Hu L. Org. Lett. 2 (2000) 1959
78. Iranpoor N., Firouzabadi H., Akhlaghinia B., and Nowrouzi N. Tetrahedron Lett. 45 (2004) 3291
79. Very recently, azidation of tert-alcohols bearing an α-ester groups was reported. See. Green J.E., Bender D.M., Jackson S., O'Donnell M.J., and McCarthy J.R. Org. Lett. 11 (2009) 807
80. Avenoza A., Cativiela C., Corzana F., Peregrina J., and Zurbano M. J. Org. Chem. 64 (1999) 8220