SCOPUS 정보 검색 플랫폼

Journal of the American Chemical Society

Volumn 124, Issue 7, 2002, Pages 1307-1315

Highly selective hydrolytic kinetic resolution of terminal epoxides catalyzed by chiral (salen)CoIII complexes. Practical synthesis of enantioenriched terminal epoxides and 1,2-diols

(8) Schaus, Scott E a Brandes, Bridget D a Larrow, Jay F a Tokunaga, Makoto a Hansen, Karl B a Gould, Alexandra E a Furrow, Michael E a Jacobsen, Eric N a

a HARVARD UNIVERSITY (United States)

Author keywords

[No Author keywords available]

Indexed keywords

HYDROLYTIC KINETIC RESOLUTION (HKR);

ALCOHOLS; CATALYSIS; COMPLEXATION; ELECTRONIC STRUCTURE; HYDROLYSIS;

OXIDES;

COBALT COMPLEX; EPOXIDE; WATER;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; CHIRALITY; ENANTIOMER; HYDROLYSIS; RACEMIC MIXTURE; STEREOCHEMISTRY; SYNTHESIS;

ALCOHOLS; CATALYSIS; CHELATING AGENTS; COBALT; EPOXY COMPOUNDS; ETHYLENEDIAMINES; HYDROLYSIS; KINETICS; STEREOISOMERISM; SUBSTRATE SPECIFICITY;

EID: 0037138704 PISSN: 00027863 EISSN: None Source Type: Journal
DOI: 10.1021/ja016737l Document Type: Article

Times cited : (983)

References (108)

1
- 0000230330
- (1961) J. Am. Chem. Soc. , vol.83 , pp. 3096
- Tarbell, D.S.¹ Carman, R.M.² Chapman, D.D.³ Cremer, S.E.⁴ Cross, A.D.⁵ Huffman, K.R.⁶ Kuntsmann, M.⁷ McCorkindale, N.J.⁸ McNally, J.G.⁹ Rosowsky, A.¹⁰ Varino, F.H.L.¹¹ West, R.L.¹²

2
- 0014224589
- (1968) Helv. Chim. Acta. , vol.51 , pp. 1395
- Sigg, H.P.¹ Weber, H.P.²

3
- 0014516488
- (1969) J. Antibiot. , vol.22 , pp. 215
- Takeuchi, T.¹ Iinuma, H.² Iwanaga, J.³ Takahashi, S.⁴ Takita, T.⁵ Umezawa, H.⁶

4
- 0014930422
- (1970) Science , vol.170 , pp. 87
- Bierl, B.A.¹ Beroza, M.² Collier, C.W.³

5
- 0015494046
- (1972) J. Am. Chem. Soc. , vol.94 , pp. 7194
- Kupchan, S.M.¹ Court, W.A.² Dailey, R.G.³ Gilmore, C.J.⁴ Bryan, R.F.⁵

6
- 2042420085
- (1976) J. Tetrahedron Lett. , vol.17 , pp. 2055
- Periplanone, B.¹ Persoons, C.J.² Verwiel, P.E.J.³ Ritter, F.J.⁴ Talman, E.⁵ Nooijen, P.J.⁶ Nooijen, W.⁷

7
- 0021960376
- (1985) Tetrahedron Lett. , vol.26 , pp. 331
- Edo, K.¹ Mizugaki, M.² Koide, Y.³ Seto, H.⁴ Furihata, K.⁵ Otake, N.⁶ Ishida, N.⁷

8
- 0025673805
- (1990) J. Antibiot. , vol.43 , pp. 1524
- Itazaki, H.¹ Nagashima, K.² Sugita, K.³ Yoshida, H.⁴ Kawamura, Y.⁵ Yasuda, Y.⁶ Matsumoto, K.⁷ Ishii, K.⁸ Uotani, N.⁹ Nakai, H.¹⁰ Terui, A.¹¹ Yoshimatsu, S.¹²

9
- 0029049468
- (1995) Cancer Res. , vol.55 , pp. 2325
- Bollag, D.M.¹ McQueney, P.A.² Zhu, J.³ Hensens, O.⁴ Koupal, L.⁵ Liesch, J.⁶ Goetz, M.⁷ Lazarides, E.⁸ Woods, C.M.⁹

10
- 0031054453
- (1997) J. Antibiot. , vol.50 , pp. 96
- Nakajima, H.¹ Takase, S.² Terano, H.³ Tanaka, H.⁴

11
- 0004246795
- Elderfield, R. C., Ed. Wiley: New York
- (1950) Heterocyclic Compounds , vol.1
- Winstein, S.¹ Henderson, R.B.²

12
- 33947470048
- (1959) Chem. Rev. , vol.59 , pp. 737
- Parker, R.E.¹ Isaacs, N.S.²

13
- 0011257113
- Small ring heterocycles
- Part 3; Hassner, A., Ed.; Wiley: New York; Chapter 1
- (1985) The Chemistry of Heterocyclic Compounds , vol.42
- Bartók, M.¹ Láng, K.L.²

14
- 0000473902
- (1983) Tetrahedron , vol.39 , pp. 2323
- Rao, A.S.¹ Paknikar, S.K.² Kirtane, J.G.³

15
- 2042520335
- (1984) Synthesis , vol.629
- Smith, J.G.¹

16
- 0000133034
- (1987) Tetrahedron Lett. , vol.28 , pp. 1993
- Larchevêque, M.¹ Petit, Y.²

17
- 0025039788
- (1990) Tetrahedron , vol.46 , pp. 4277
- Larchevêque, M.¹ Henrot, S.²

18
- 0028835948
- (1995) Synth. Commun. , vol.25 , pp. 331
- De March, P.¹ Figueredo, M.² Font, J.³ Monsalvatje, M.⁴

19
- 0029131054
- (1995) Tetrahedron Lett. , vol.36 , pp. 7367
- Adiyaman, M.¹ Khanapure, S.P.² Hwang, S.W.³ Rokach, J.⁴

20
- 2042522960
- Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds. Springer: New York; Chapter 18.1
- (1999) Comprehensive Asymmetric Catalysis
- Katsuki, T.¹

21
- 0000316792
- Morrison, J, D., Ed.; Academic Press: New York; Chapter 7
- (1985) Asymmetric Synthesis , vol.5
- Rossiter, B.E.¹

22
- 0003544583
- Ojima, I., Ed.; VCH: New York; Chapter 4.1
- (1993) Catalytic Asymmetric Synthesis
- Johnson, R.A.¹ Sharpless, K.B.²

23
- 0001780886
- (1996) Org. React. , vol.48 , pp. 1
- Katsuki, T.¹ Martin, V.S.²

24
- 0003445429
- Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: New York; Chapter 18.2
- (1999) Comprehensive Asymmetric Catalysis
- Jacobsen, E.N.¹ Wu, M.H.²

25
- 0000775309
- (1995) Coord Chem. Rev. , vol.140 , pp. 189
- Katsuki, T.¹

26
- 0001405437
- Wilkinson, G., Stone, F. G. A., Abel, E. W., Hegedus, L. S., Eds.; Pergamon: New York
- (1995) Comprehensive Organometallic Chemistry II , vol.12 , pp. 1097-1135
- Jacobsen, E.N.¹

27
- 0034536438
- (2000) Synthesis , pp. 1979
- Frohn, M.¹ Shi, Y.²

28
- 0026495369
- (1992) Tetrahedron , vol.48 , pp. 10515
- Kolb, H.C.¹ Sharpless, K.B.²

29
- 0000710639
- (1991) Tetrahedron Lett. , vol.56 , pp. 442
- Corey, E.J.¹ Link, J.O.²

30
- 0027226259
- (1993) Tetrahedron Lett. , vol.34 , pp. 5227
- Corey, E.J.¹ Helal, C.J.²

31
- 0001939466
- (1995) J. Org. Chem. , vol.60 , pp. 41
- Ramachandran, P.V.¹ Gong, B.² Brown, H.C.³

32
- 0028902830
- (1995) J. Am. Chem. Soc. , vol.117 , pp. 2931
- Kitamura, M.¹ Tokunaga, M.² Noyori, R.³

33
- 0001580728
- (1994) J. Am. Chem. Soc. , vol.116 , pp. 9333
- Palucki, M.¹ Pospisil, P.J.² Zhang, W.³ Jacobsen, E.N.⁴

34
- 0033585578
- (1999) J. Am. Chem. Soc. , vol.121 , pp. 460
- Collman, J.P.¹ Wang, Z.² Straumanis, A.³ Quelquejeu, M.⁴ Rose, E.⁵

35
- 0033406673
- and references therein
- (1999) Tetrahedron Assymetry , vol.10 , pp. 3327
- Botes, A.L.¹ Weijers, C.A.G.M.² Botes, P.J.³ Van Dyk, M.S.⁴

36
- 0033551906
- and references therein
- (1999) Tetrahedron: Asymmetry , vol.10 , pp. 3167
- Goswami, A.¹ Totleben, M.J.² Singh, A.K.³ Patel, R.N.⁴

37
- 18844410382
- (1987) J. Am. Chem. Soc. , vol.109 , pp. 5765
- Gao, Y.¹ Klunder, J.M.² Hanson, R.M.³ Masamune, H.⁴ Ko, S.Y.⁵ Sharpless, K.B.⁶

38
- 33845470686
- (1984) J. Am. Chem. Soc. , vol.106 , pp. 7250
- Ladner, W.E.¹ Whitesides, G.M.²

39
- 0000830825
- (1991) Chem. Rev. , vol.91 , pp. 437
- Hanson, R.M.¹

40
- 0026599226
- (1992) Tetrahedron Lett. , vol.33 , pp. 1211
- Kasai, N.¹ Sakaguchi, K.²

41
- 0345664754
- (1995) J. Am. Chem. Soc. , vol.117 , pp. 5897
- Martínez, L.E.¹ Leighton, J.L.² Carsten, D.H.³ Jacobsen, E.N.⁴

42
- 0031024261
- (1997) Tetrahedron Lett. , vol.38 , pp. 773
- Jacobsen, E.N.¹ Kakiuchi, F.² Konsler, R.G.³ Larrow, J.F.⁴ Tokunaga, M.⁵

43
- 0001044547
- (1998) J. Org. Chem. , vol.63 , pp. 5252
- Wu, M.H.¹ Jacobsen, E.N.²

44
- 0034611489
- (2000) Org. Lett. , vol.2 , pp. 1001
- Schaus, S.E.¹ Jacobsen, E.N.²

45
- 0003942864
- Wiley: New York; Chapter 7.6
- (1994) Stereochemistry of Organic Compounds
- Eliel, E.L.¹ Wilen, S.H.²

46
- 0002178750
- (2001) Adv. Synth. Catal. , vol.343 , pp. 5-26
- Keith, J.M.¹ Larrow, J.F.² Jacobsen, E.N.³

47
- 0030860279
- (1997) Science , vol.277 , pp. 936
- Tokunaga, M.¹ Larrow, J.F.² Kakiuchi, F.³ Jacobsen, E.N.⁴

48
- 0000180260
- (1998) J. Org. Chem. , vol.63 , pp. 6776
- Furrow, M.E.¹ Schaus, S.E.² Jacobsen, E.N.³

49
- 0008521403
- (1980) Tetrahedron , vol.36 , pp. 3391
- Tekeichi, T.¹ Arihara, M.² Ishimori, M.³ Tsuruta, T.⁴

50
- 0026259466
- (1991) React. Kinet. Catal. Lett. , vol.45 , pp. 165
- Maruyama, K.¹ Nakamura, T.² Nakamura, S.³ Ogino, A.⁴ Nishinaga, A.⁵

51
- 0029757771
- (1996) J. Am. Chem. Soc. , vol.118 , pp. 7420
- Larrow, J.F.¹ Schaus, S.E.² Jacobsen, E.N.³

52
- 4243525589
- (1998) Trends Biotechnol. , vol.16 , pp. 08
- Archelas, A.¹ Furstoss, R.²

53
- 33750368763
- (1994) J. Org. Chem. , vol.59 , pp. 1939
- Larrow, J.F.¹ Jacobsen, E.N.² Gao, Y.³ Hong, Y.⁴ Nie, X.⁵ Zepp, C.M.⁶

54
- 0002504397
- (1997) Org. Synth. , vol.75 , pp. 1
- Larrow, J.F.¹ Jacobsen, E.N.²

55
- 2042450227

56
- 2042425758
- note

57
- 33750247077
- (1996) Angew. Chem., Int. Ed. Engl. , vol.35 , pp. 448
- Becker, H.¹ Sharpless, K.B.²

58
- 4444276636
- (1994) Chem. Rev. , vol.94 , pp. 2483
- Kolb, H.C.¹ VanNieuwenhze, M.S.² Sharpless, K.B.³

59
- 0031843545
- (1998) J. Org. Chem. , vol.63 , pp. 4876
- Schaus, S.E.¹ Brånalt, J.E.² Jacobsen, E.N.³

60
- 0032486157
- (1998) Tetrahedron: Asymmetry , vol.9 , pp. 1843
- Savle, P.S.¹ Lamoreaux, M.J.² Berry, J.F.³ Gandour, R.D.⁴

61
- 0001077618
- (1998) Heterocyctes , vol.48 , pp. 1471
- Gurjar, M.K.¹ Sadalapure, K.² Adhikari, S.³ Sarma, B.V.N.B.S.⁴ Talukdar, A.⁵ Chorghade, M.S.⁶

62
- 15444362956
- (1998) Org. Proc. Res. Dev. , vol.2 , pp. 422
- Gurjar, M.K.¹ Krishna, L.M.² Sarma, B.V.N.B.S.³ Chorghade, M.S.⁴

63
- 0033540691
- (1999) J. Am. Chem. Soc. , vol.121 , pp. 1092
- Cloninger, M.J.¹ Overman, L.E.²

64
- 0033538635
- (1999) Tetrahedron Lett. , vol.40 , pp. 5161
- Rodríguez, A.¹ Nomen, M.² Spur, B.W.³ Godfroid, J.J.⁴

65
- 0033580767
- (1999) Tetrahedron: Asymmetry , vol.10 , pp. 2319
- Hou, X.-L.¹ Li, B.-F.² Dai, L.-X.³

66
- 0033452450
- (1999) Tetrahedron: Asymmetry , vol.10 , pp. 3667
- Kamada, M.¹ Satoh, T.² Kakuchi, T.³ Yokota, K.⁴

67
- 2042467812
- (1999) Chem. Commun. , vol.129
- Yu, Q.¹ Wu, Y.² Xia, L.-J.³ Tang, M.-H.⁴ Wu, Y.-L.⁵

68
- 0033609773
- (1999) Tetrahedron Lett. , vol.40 , pp. 6481
- Wyatt, P.B.¹ Blakskjær, P.²

69
- 0034673315
- (2000) J. Am. Chem. Soc. , vol.122 , pp. 1235
- Liu, P.¹ Panek, J.S.²

70
- 0038741422
- (2000) Tetrahedron Lett. , vol.41 , pp. 1171
- Knölker, H.-J.¹ Baum, E.² Reddy, K.R.³

71
- 0038065000
- (2000) Tetrahedron: Asymmetry , vol.11 , pp. 2053
- Wroblewski, A.E.¹ Halajewska-Wosik, A.²

72
- 85047680712
- (2000) J. Chem. Soc., Perkin Trans. 1 , pp. 3519
- Liu, Z.Y.¹ Ji, J.X.² Li, B.G.³

73
- 0034032708
- (2000) Synlett , pp. 695
- O'Neil, I.A.¹ Cleator, E.² Southern, J.M.³ Hone, N.⁴ Tapolczay, D.J.⁵

74
- 0035825762
- (2001) Org. Lett. , vol.3 , pp. 449
- Fürstner, A.¹ Thiel, O.R.² Ackermann, L.³

75
- 0035821998
- (2001) Chem. Commun. , pp. 1040
- Chow, S.¹ Kitching, W.²

76
- 0035056012
- (2001) Tetrahedron , vol.57 , pp. 25
- Rodriguez, A.¹ Nomen, M.² Spur, B.W.³ Godfroid, J.J.⁴ Lee, T.H.⁵

77
- 2042495718
- note

78
- 2042528731
- note

79
- 0001477570
- Paquette, L. A. Ed.; Wiley: New York
- (1995) Encyclopedia of Reagents for Organic Synthesis , vol.4 , pp. 2326
- Huber, J.E.¹

80
- 0034632397
- and references therein
- (2000) Org. Lett. , vol.2 , pp. 2423
- Katagiri, T.¹ Irie, M.² Uneyama, K.³

81
- 0022973828
- (1986) J. Org. Chem. , vol.51 , pp. 3710
- Klunder, J.M.¹ Ko, S.Y.² Sharpless, K.B.³

82
- 2042459406
- note

83
- 0035477040
- (2001) Angew. Chem., Int. Ed. , vol.40 , pp. 3667
- Chavez, D.E.¹ Jacobsen, E.N.²

84
- 0031465950
- (1997) Tetrahedron: Asymmetry , vol.8 , pp. 3927
- Brandes, B.D.¹ Jacobsen, E.N.²

85
- 0000058426
- Grasselli, R. K., Oyama, S. T., Gaffney, A. M., Lyons, J. E., Eds.; Elsevier: New York
- (1997) 3rd World Congress on Oxidation Catalysis , pp. 135-149
- Monnier, J.R.¹

86
- 0033595445
- (1999) J. Am. Chem. Soc. , vol.121 , pp. 8649
- Trost, B.M.¹ McEachem, E.J.²

87
- 18844410382
- (1987) J. Am. Chem. Soc. , vol.109 , pp. 5765
- Gao, Y.¹ Hanson, R.M.² Klunder, J.M.³ Ko, S.Y.⁴ Masamune, H.⁵ Sharpless, K.B.⁶

88
- 0033618105
- (1999) J. Am. Chem. Soc. , vol.121 , pp. 6086
- Ready, J.M.¹ Jacobsen, E.N.²

89
- 0002923489
- (1995) Bull. Chem. Soc. Jpn. , vol.68 , pp. 36
- Noyori, R.¹ Tokunaga, M.² Kitamura, M.³

90
- 0033556602
- (1999) Tetrahedron Asymmetry , vol.10 , pp. 107
- Strauss, U.T.¹ Felfer, U.²

91
- 0033023975
- (1999) Curr. Opin. Chem. Biol. , vol.3 , pp. 11
- El Gihani, M.T.¹ Williams, J.M.J.²

92
- 1842378180
- Eliel, E. L., Wilen, S. H., Eds.; Wiley: New York
- (1987) Topics in Stereochemistry , vol.14 , pp. 249-330
- Kagan, H.B.¹ Fiaud, J.C.²

93
- 0030900381
- (1997) Chem. Eur. J. , vol.3 , pp. 517
- Vanhessche, K.P.M.¹ Sharpless, K.B.²

94
- 0002923489
- (1995) Bull. Chem. Soc. Jpn. , vol.68 , pp. 36
- Noyori, R.¹ Tokunaga, M.² Kitamura, M.³

95
- 2042466158
- note

96
- 0033552241
- (1999) J. Am. Chem. Soc. , vol.121 , pp. 9299
- Luukas, T.O.¹ Girard, C.² Fenwick, D.R.³ Kagan, H.B.⁴

97
- 0040292267
- (1999) J. Am. Chem. Soc. , vol.121 , Issue.1 , pp. 9307
- Johnson Jr., D.W.¹ Singleton, D.A.²

98
- 0035977603
- (2001) J. Am. Chem. Soc. , vol.123 , pp. 545
- Blackmond, D.G.¹

99
- 2042522111
- note

100
- 2042532064
- note

101
- 0029798420
- (1996) J. Am. Chem. Soc. , vol.118 , pp. 10924
- Hansen, K.B.¹ Leighton, J.L.² Jacobsen, E.N.³

102
- 0031704998
- (1998) Angew. Chem., Int. Ed. Engl. , vol.37 , pp. 2223
- Iida, T.¹ Yamamoto, N.² Matsunaga, S.³ Woo, H.-G.⁴ Shibasaki, M.⁵

103
- 0000931779
- (1998) J. Org. Chem. , vol.63 , pp. 6656
- McCleland, B.W.¹ Nugent, W.A.² Finn, M.G.³

104
- 0033526360
- (1999) J. Am. Chem. Soc. , vol.121 , pp. 4147
- Annis, D.A.¹ Jacobsen, E.N.²

105
- 0034675617
- (2000) Angew. Chem., Int. Ed. , vol.39 , pp. 3604
- Breinbauer, R.¹ Jacobsen, E.N.²

106
- 0034833453
- (2001) J. Am. Chem. Soc. , vol.123 , pp. 2687
- Ready, J.M.¹ Jacobsen, E.N.²

107
- 0033536712
- (1999) Tetrahedron Lett. , vol.40 , pp. 7303
- Lebel, H.¹ Jacobsen, E.N.²

108
- 0002504397
- Also available commercially (Aldrich)
- (1997) Org. Synth. , vol.75 , pp. 1
- Larrow, J.F.¹ Jacobsen, E.N.²

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.