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Journal of the American Chemical Society

Volumn 123, Issue 42, 2001, Pages 10191-10199

Metal ion-catalyzed cycloaddition vs hydride transfer reactions of NADH analogues with p-benzoquinones

(3) Fukuzumi, S a,b Fujii, Y a,b Suenobu, T a,b

a OSAKA UNIVERSITY (Japan)

b JAPAN SCIENCE AND TECHNOLOGY AGENCY (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ELECTRON TRANSFER;

CATALYSIS; CRYSTAL STRUCTURE; SCANDIUM COMPOUNDS; THERMAL EFFECTS; X RAY CRYSTALLOGRAPHY;

AROMATIC COMPOUNDS;

BENZOQUINONE; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE;

ARTICLE; CATALYSIS; CRYSTAL STRUCTURE; ELECTRON TRANSPORT; HYDROGEN BOND; HYDROLYSIS; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; X RAY CRYSTALLOGRAPHY;

BENZOQUINONES; HYDROGEN; NAD; SCANDIUM;

EID: 0035944441 PISSN: 00027863 EISSN: None Source Type: Journal
DOI: 10.1021/ja016370k Document Type: Article

Times cited : (79)

References (118)

1
- 0007213364
- (1972) Chem. Rev. , vol.72 , pp. 1
- Eisner, U.¹ Kuthan, J.²

2
- 33745485017
- (1982) Chem. Rev. , vol.82 , pp. 223
- Stout, D.M.¹ Meyers, A.I.²

3
- 0004051998
- Walter de Gruyer: West Berlin, Germany
- (1977) Pyridine-Nucleotide Dependent Dehydrogenase
- Sund, H.¹

4
- 0020012174
- (1982) Top. Curr. Chem. , vol.101 , pp. 111
- Kellog, R.M.¹

5
- 0000337159
- (1984) Angew. Chem. , vol.96 , pp. 769
- Kellog, R.M.¹

6
- 0003542841
- Springer-Verlag: Berlin, Germany
- (1986) Lecture Notes in Bioorganic Chemistry, Mechanistic Models of Asymmetric Reductions , pp. 105
- Ohno, A.¹ Ushida, S.²

7
- 0001548808
- (1991) Bioorg. Chem. , vol.19 , pp. 456
- Bunting, J.W.¹

8
- 0027732515
- (1993) Bioorg. Chem. , vol.21 , pp. 423
- He, G.-X.¹ Blasko, A.² Bruice, T.C.³

9
- 0000332466
- (1995) J. Phys. Org. Chem. , vol.8 , pp. 567
- Ohno, A.¹

10
- 0001950984
- Mariano, P. S., Ed.; JAI Press Greenwich, CT
- (1992) Advances in Electron-Transfer Chemistry , pp. 67-175
- Fukuzumi, S.¹

11
- 0004186505
- Fox, M. A., Chanon, M., Eds.; Elsevier: Amsterdam, The Netherlands, Part C, Chapter 10
- (1988) Photoinduced Electron Transfer
- Fukuzumi, S.¹ Tanaka, T.²

12
- 0347852563
- (1987) J. Am. Chem. Soc. , vol.109 , pp. 305
- Fukuzumi, S.¹ Koumitsu, S.² Hironaka, K.³ Tanaka, T.⁴

13
- 0000025341
- (1989) J. Am. Chem. Soc. , vol.111 , pp. 1497
- Fukuzumi, S.¹ Mochizuki, S.² Tanaka, T.³

14
- 0000477843
- (1990) J. Am. Chem. Soc. , vol.112 , pp. 5631
- Fukuzumi, S.¹ Kitano, T.² Ishikawa, M.³

15
- 0001416648
- (1993) J. Am. Chem. Soc. , vol.115 , pp. 8960
- Fukuzumi, S.¹ Tokuda, Y.² Kitano, T.³ Okamoto, T.⁴ Otera, J.⁵

16
- 0034630893
- (2000) J. Am. Chem. Soc. , vol.122 , pp. 4286
- Fukuzumi, S.¹ Ohkubo, K.² Tokuda, Y.³ Suenobu, T.⁴

17
- 0001274252
- (1998) J. Org. Chem. , vol.63 , pp. 6108
- Cheng, J.-P.¹ Lu, Y.² Zhu, X.³ Mu, L.⁴

18
- 0032583444
- (1998) J. Am. Chem. Soc. , vol.120 , pp. 13422
- Pestovsky, O.¹ Bakac, A.² Espenson, J.H.³

19
- 0001099145
- (1992) J. Am. Chem. Soc. , vol.114 , pp. 9755
- Coleman, C.A.¹ Rose, J.G.² Murray, C.J.³

20
- 0000910517
- (1991) J. Am. Chem. Soc , vol.113 , pp. 7426
- Murray, C.J.¹ Webb, T.²

21
- 0000910187
- (1993) J. Org. Chem. , vol.58 , pp. 5050
- Cheng, J.-P.¹ Handoo, K.L.² Xue, J.³ Parker, V.D.⁴

22
- 0000524673
- (1984) J. Am. Chem. Soc. , vol.106 , pp. 7233
- Carlson, B.W.¹ Miller, L.L.² Neta, P.³ Grodkowski, J.⁴

23
- 0001295764
- (1984) J. Am. Chem. Soc. , vol.106 , pp. 3850
- Powell, M.F.¹ Wu, J.C.² Bruice, T.C.³

24
- 0000725558
- (1984) J. Am. Chem. Soc. , vol.106 , pp. 7291
- Sinha, A.¹ Bruice, T.C.²

25
- 0000432607
- (1990) Can. J. Chem. , vol.68 , pp. 1662
- Tanner, D.D.¹ Kharrat, A.² Oumar-Mahamat, H.³

26
- 0001243450
- (1988) J. Org. Chem. , vol.53 , pp. 1646
- Tanner, D.D.¹ Kharrat, A.²

27
- 0029088060
- (1995) Tetrahedron , vol.51 , pp. 9671
- Liu, Y.-C.¹ Li, B.² Guo, Q.-X.³

28
- 0032542585
- (1998) J. Am. Chem. Soc. , vol.120 , pp. 1186
- Ohno, A.¹ Ishikawa, Y.² Yamazaki, N.³ Okamura, M.⁴ Kawai, Y.⁵

29
- 0030739041
- (1997) Angew. Chem., Int. Ed. Engl. , vol.36 , pp. 1207
- Kanomata, N.¹ Nakata, T.²

30
- 0032486327
- (1998) Angew. Chem., Int. Ed. Engl. , vol.37 , pp. 1410
- Kanomata, N.¹ Suzuki, M.² Yoshida, M.³ Nakata, T.⁴

31
- 0034680589
- (2000) Angew. Chem. Int. Ed. , vol.39 , pp. 4061
- Konno, H.¹ Sakamoto, K.² Ishitani, O.³

32
- 33845280944
- (1988) J. Am. Chem. Soc. , vol.110 , pp. 524
- Kreevoy, M.M.¹ Ostović, D.² Lee, I.-S.H.³ Binder, D.A.⁴ King, G.W.⁵

33
- 0030887229
- (1997) J. Am. Chem. Soc. , vol.119 , pp. 2722
- Lee, I.-S.H.¹ Jeoung, E.H.² Kreevoy, M.M.³

34
- 0032053614
- (1998) J. Am. Chem. Soc. , vol.120 , pp. 2951
- Anne, A.¹ Fraoua, S.² Grass, V.³ Moiroux, J.⁴ Savéant, J.-M.⁵

35
- 0029929090
- (1996) J. Am. Chem. Soc. , vol.118 , pp. 3938
- Anne, A.¹ Fraoua, S.² Moiroux, J.³ Savéant, J.-M.⁴

36
- 0029097060
- (1995) J. Am. Chem. Soc. , vol.117 , pp. 7412
- Anne, A.¹ Fraoua, S.² Hapiot, P.³ Moiroux, J.⁴ Savéant, J.-M.⁵

37
- 0025317253
- (1990) J. Am. Chem. Soc. , vol.112 , pp. 1337
- Hapiot, P.¹ Moiroux, J.² Savéant, J.-M.³

38
- 0000980070
- (1991) J. Phys. Chem. , vol.95 , pp. 2370
- Anne, A.¹ Hapiot, P.² Moiroux, J.³ Neta, P.⁴ Savéant, J.-M.⁵

39
- 0000885217
- (1992) J. Am. Chem. Soc. , vol.114 , pp. 4694
- Anne, A.¹ Hapiot, P.² Moiroux, J.³ Neta, P.⁴ Savéant, J.-M.⁵

40
- 0001200963
- (1993) J. Am. Chem. Soc. , vol.115 , pp. 10224
- Anne, A.¹ Moiroux, J.² Savéant, J.-M.³

41
- 0000303985
- (1988) J. Am. Chem. Soc. , vol.110 , pp. 3982
- Miller, L.L.¹ Valentine, J.R.²

42
- 0001505697
- (1991) J. Org. Chem. , vol.56 , pp. 6736
- Klippenstein, J.¹ Arya, P.² Wayner, D.D.M.³

43
- 0001467919
- (1986) J. Org. Chem. , vol.51 , pp. 2060
- Bunting, J.W.¹ Stefanidis, D.²

44
- 0001377673
- (1985) J. Am. Chem. Soc. , vol.107 , pp. 479
- Carlson, B.W.¹ Miller, L.L.²

45
- 0031260208
- (1997) J. Am. Chem. Soc. , vol.119 , pp. 9114
- Bardea, A.¹ Katz, E.² Bückmann, A.F.³ Willner, I.⁴

46
- 0001110215
- van Tamelen, E. E., Ed.; Academic Press: New York
- (1978) Bioorganic Chemistry , vol.4 , pp. 385
- Sigman, D.S.¹ Hajdu, J.² Creighton, D.J.³

47
- 0000360667
- (1979) J. Am. Chem. Soc. , vol.101 , pp. 7059
- Gase, R.A.¹ Pandit, U.K.²

48
- 0000510205
- (1981) J. Am. Chem. Soc. , vol.103 , pp. 2041
- Ohno, A.¹ Yamamoto, H.² Oka, S.³

49
- 0000418611
- (1981) J. Am. Chem. Soc. , vol.103 , pp. 2045
- Ohno, A.¹ Shio, T.² Yamamoto, H.³ Oka, S.⁴

50
- 37049104782
- (1985) J. Chem. Soc., Perkin Trans. 2 , pp. 371
- Fukuzumi, S.¹ Nishizawa, N.² Tanaka, T.³

51
- 0001527776
- (1990) J. Chem. Soc., Faraday Trans. , vol.86 , pp. 3531
- Ishikawa, M.¹ Fukuzumi, S.²

52
- 0002649758
- (1997) Bull. Chem. Soc. Jpn. , vol.70 , pp. 1
- Fukuzumi, S.¹

53
- 0001164758
- Neckers, D. C., Volman, D. H., von Bünau, G., Eds.; Wiley: New York
- (1998) Advances in Photochemistry , vol.25 , pp. 107-172
- Fukuzumi, S.¹ Itoh, S.²

54
- 0002636202
- Balzani, V., Ed.; Wiley-VCH: Weinheim, Germany
- (2001) Electron Transfer in Chemistry , vol.4 , pp. 3-59
- Fukuzumi, S.¹

55
- 12044249612
- (1993) J. Am. Chem. Soc. , vol.115 , pp. 11600
- Fukuzumi, S.¹ Okamoto, T.²

56
- 0032578160
- (1998) J. Am. Chem. Soc. , vol.120 , pp. 7271
- Itoh, S.¹ Kawakami, H.² Fukuzumi, S.³

57
- 0031054851
- (1997) J. Am. Chem. Soc. , vol.119 , pp. 439
- Itoh, S.¹ Kawakami, H.² Fukuzumi, S.³

58
- 0032485844
- (1998) Biochemistry , vol.37 , pp. 6562
- Itoh, S.¹ Kawakami, H.² Fukuzumi, S.³

59
- 1842384151
- (1994) J. Am. Chem. Soc. , vol.116 , pp. 5503
- Fukuzumi, S.¹ Okamoto, T.² Otera, J.³

60
- 0002452485
- Fox, M. A., Chanon, M., Eds.; Elsevier: Amsterdam, The Netherlands; Part C, Chapter 11
- (1988) Photoinduced Electron Transfer , pp. 636-687
- Fukuzumi, S.¹ Tanaka, T.²

61
- 0007562550
- (1986) Tetrahedron , vol.42 , pp. 6573
- Kagan, H.B.¹ Namy, J.L.²

62
- 0010077452
- (1992) Chem. Rev. , vol.92 , pp. 29
- Molander, G.A.¹

63
- 0003537151
- Katritzky, A. R., Meth-Cohn, O., Rees, C. W., Eds.; Academic Press: London, UK
- (1994) Lanthanides in Organic Synthesis
- Imamoto, T.¹

64
- 85064667331
- (1994) Synlett , pp. 689
- Kobayashi, S.¹

65
- 12044259576
- (1995) Aldrichim. Acta , vol.28 , pp. 77
- Marshmann, R.W.¹

66
- 0002897061
- Yoshida, Z., Shiba, T., Ohshiro, Y., Eds.; VCH: New York, Chapter 4
- (1989) New Aspects of Organic Chemistry , pp. 55
- Inanaga, J.¹ Yamaguchi, M.²

67
- 2142715741
- (1996) Chem. Rev. , vol.96 , pp. 307
- Molander, G.A.¹ Harris, C.R.²

68
- 0030788440
- (1997) Angew. Chem., Int. Ed. Engl. , vol.36 , pp. 1236
- Shibasaki, M.¹ Sasai, H.² Arai, T.³

69
- 0032547286
- (1998) J. Am. Chem. Soc. , vol.120 , pp. 8287
- Kobayashi, S.¹ Nagayama, S.² Busujima, T.³

70
- 0001045470
- (1994) J. Am. Chem. Soc. , vol.116 , pp. 4083
- Kobayashi, S.¹ Ishitani, H.²

71
- 0028217046
- (1994) Tetrahedron Lett. , vol.35 , pp. 2771
- Markó, I.E.¹ Evans, G.R.²

72
- 0002897799
- (1996) Chem. Commun. , pp. 183
- Kawada, A.¹ Mitamura, S.² Kobayashi, S.³

73
- 0000082453
- (1994) J. Org. Chem. , vol.59 , pp. 3758
- Kobayashi, S.¹ Araki, M.² Hachiya, I.³

74
- 0012615648
- (1996) J. Org. Chem. , vol.61 , pp. 4560
- Ishihara, K.¹ Kubota, M.² Kurihara, H.³ Yamamoto, H.⁴

75
- 85011245852
- (1995) J. Am. Chem. Soc. , vol.117 , pp. 4413
- Ishihara, K.¹ Kubota, M.² Kurihara, H.³ Yamamoto, H.⁴

76
- 0000779953
- (1998) J. Am. Chem. Soc. , vol.120 , pp. 2985
- Kobayashi, S.¹ Nagayama, S.²

77
- 0027262676
- (1993) Tetrahedron Lett. , vol.34 , pp. 3755
- Kobayashi, S.¹ Hachiya, I.² Araki, M.³ Ishitani, H.⁴

78
- 0002814660
- (1994) Synlett , pp. 689
- Kawada, A.¹ Mitamura, S.² Kobayashi, S.³

79
- 37049070092
- (1995) J. Chem. Soc. Chem. Commun. , pp. 1527
- Kobayashi, S.¹ Moriwaki, M.² Hachiya, I.³

80
- 0001017480
- (1996) J. Org. Chem. , vol.61 , pp. 2256
- Kobayashi, S.¹ Nagayama, S.²

81
- 0029813591
- (1996) J. Am. Chem. Soc. , vol.118 , pp. 8977
- Kobayashi, S.¹ Nagayama, S.²

82
- 0030581392
- (1996) Tetrahedron , vol.52 , pp. 11045
- Bisi Castellani, C.¹ Carugo, O.² Giusti, M.³ Leopizzi, C.⁴ Perotti, A.⁵ Invernizzi Gamba, A.⁶ Vidari, G.⁷

83
- 0040561956
- (1998) Angew. Chem., Int. Ed. Engl. , vol.37 , pp. 2259
- Lacôte, E.¹ Renaud, P.²

84
- 0000699250
- (1998) Heterocycles , vol.48 , pp. 1649
- Hilgeroth, A.¹ Kuna, K.² Kuckländer, U.³

85
- 0035308887
- (2001) Heterocycles , vol.55 , pp. 661
- Hilgeroth, A.¹ Brachwitz, K.² Baumeister, U.³

86
- 0000003267
- (1979) J. Am. Chem. Soc. , vol.101 , pp. 7406
- Van Eikeren, P.¹ Grier, D.L.² Eliason, J.³

87
- 0014301097
- (1968) Biochemistry , vol.7 , pp. 2339
- Kim, C.S.Y.¹ Chaykin, S.²

88
- 0000225521
- (1986) Tetrahedron , vol.42 , pp. 1021
- Fukuzumi, S.¹ Ishikawa, M.² Tanaka, T.³

89
- 0002724210
- (1976) Tetrahedron Lett. , pp. 2541
- Tagaki, W.¹ Sakai, H.² Yano, Y.³ Ozeki, K.⁴ Shimizu, Y.⁵

90
- 0020847255
- (1983) J. Am. Chem. Soc. , vol.105 , pp. 7139
- Powell, M.F.¹ Bruice, T.C.²

91
- 0347852563
- (1987) J. Am. Chem. Soc. , vol.109 , pp. 305
- Fukuzumi, S.¹ Koumitsu, S.² Hironaka, K.³ Tanaka, T.⁴

92
- 33947464527
- (1958) J. Am. Chem. Soc. , vol.80 , pp. 992
- Anderson A.G., Jr.¹ Berkelhammer, G.²

93
- 33947466443
- (1955) J. Am. Chem. Soc. , vol.77 , pp. 2261
- Mauzerall, D.¹ Westheimer, F.H.²

94
- 0001260994
- (1966) J. Org. Chem. , vol.31 , pp. 1978
- Caughey, W.S.¹ Schellenberg, K.A.²

95
- 0000106905
- (1992) Heterocycles , vol.34 , pp. 2331
- Anne, A.¹

96
- 0001004022
- (1996) Chem. Lett. , pp. 1103
- Takada, N.¹ Itoh, S.² Fukuzumi, S.³

97
- 84981757301
- (1959) Chem. Ber. , vol.92 , pp. 1406
- Wallenfels, K.¹ Gellerich, M.²

98
- 0031521116
- (1997) Chem. Lett. , pp. 567
- Patz, M.¹ Kuwahara, Y.² Suenobu, T.³ Fukuzumi, S.⁴

99
- 0020360650
- (1982) Inorg. Chem. , vol.21 , pp. 3420
- Shirazi, A.¹ Goff, H.M.²

100
- 0001008984
- (1987) J. Org. Chem. , vol.52 , pp. 1017
- Forsberg, J.H.¹ Spaziano, V.T.² Balasubramanian, T.M.³ Liu, G.K.⁴ Kinsley, S.A.⁵ Duckworth, C.A.⁶ Poteruca, J.J.⁷ Brown, P.S.⁸ Miller, J.L.⁹

101
- 33751157649
- (1994) J. Org. Chem. , vol.59 , pp. 3590
- Kobayashi, S.¹ Hachiya, I.²

102
- 85011648851
- (1993) Synlett , pp. 472
- Kobayashi, S.¹ Hachiya, I.² Ishitani, H.³ Araki, M.⁴

103
- 0002873274
- U.S. Patent 3615169, 1971
- Thom, K.F.¹

104
- 0007795046
- (1972) Chem. Abstr. , vol.76

105
- 0004055425
- Butterworth-Heinemann: Oxford, UK
- (1988) Purification of Laboratory Chemicals
- Perrin, D.D.¹ Armarego, W.L.F.²

106
- 0003470460
- Molecular Structure Corp.: The Woodlands, TX 77381
- (1989) TEXSAN, Single-Crystal Structure Analysis Software, Version 5.0

107
- 0000189651
- (1993) J. Chem. Phys. , vol.98 , pp. 5648-5652
- Becke, A.D.¹

109
- 0000477054
- (1963) Biochemistry , vol.2 , pp. 689
- Johnston, C.C.¹ Gardner, J.L.² Suelter, C.H.³ Metzler, D.E.⁴

110
- 37049070347
- (1986) J. Chem. Soc., Chem. Commun. , pp. 1080
- Yoon, C.-J.¹ Ikeda, H.² Kojin, R.³ Ikeda, T.⁴ Toda, F.⁵

111
- 0002873276
- note

112
- 0002807087
- note

113
- 0031521116
- (1997) Chem. Lett. , pp. 567
- Patz, M.¹ Kuwahara, Y.² Suenobu, T.³ Fukuzumi, S.⁴

114
- 0032547242
- (1998) J. Am. Chem. Soc. , vol.120 , pp. 8060
- Fukuzumi, S.¹ Suenobu, T.² Patz, M.³ Hirasaka, T.⁴ Itoh, S.⁵ Fujitsuka, M.⁶ Ito, O.⁷

115
- 0002873278
- note

116
- 0034671272
- (2000) Chem. Eur. J. , vol.6 , pp. 4532
- Fukuzumi, S.¹ Ohkubo, K.²

117
- 0002724212
- note

118
- 0002745102
- note

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