SCOPUS 정보 검색 플랫폼

Journal of the American Chemical Society

Volumn 119, Issue 46, 1997, Pages 11224-11235

An efficient catalytic asymmetric epoxidation method

(5) Wang, Zhi Xian a Tu, Yong a Frohn, Michael a Zhang, Jian Rong a Shi, Yian a

a Department of Environmental and Radiological Health Sciences (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EPOXIDE;

ARTICLE; CATALYSIS; EPOXIDATION; IN VITRO STUDY; METHODOLOGY; PH; REACTION ANALYSIS; TEMPERATURE SENSITIVITY;

EID: 0030665236 PISSN: 00027863 EISSN: None Source Type: Journal
DOI: 10.1021/ja972272g Document Type: Article

Times cited : (633)

References (93)

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

2
- 1842286445
- Ojima, I., Ed.; VCH: New York, Chapter 4.2
- (2) For more recent leading references, see: (a) Jacobsen, E. N. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: New York, 1993; Chapter 4.2. (b) Collman, J. P.; Zhang, X.; Lee, V. J.; Uffelman, E. S.; Brauman, J. I. Science 1993, 261, 1404-1411. (c) Allain, E. J.; Hager, L. P.; Deng, L.; Jacobsen, E. N. J. Am. Chem. Soc. 1993, 115, 4415-4416. (d) Brandes, B. D.; Jacobsen, E. N. J. Org. Chem. 1994, 59, 4378-4380. (e) Hosoya, N.; Hatayama, A.; Irie, R.; Sasaki, H.; Katsuki, T. Tetrahedron 1994, 50, 4311-4322. (f) Fukuda, T.; Irie, R.; Katsuki, T. Synlett 1995, 197-198. (g) Collman, J. P.; Lee, V. J.; Kellen-Yuen, C. J.; Zhang, X.; Ibers, J.A.; Brauman, J. I. J. Am. Chem. Soc. 1995, 117, 692-703. (h) Fukuda, T.; Katsuki, T. Tetrahedron Lett. 1996, 37, 4389-4392. (i) Mukaiyama T. Aldrichim. Acta 1996, 29, 59-76.
- (1993) Catalytic Asymmetric Synthesis
- Jacobsen, E.N.¹

3
- 0027424108
- For more recent leading references, see: (a) Jacobsen, E. N. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: New York, 1993; Chapter 4.2. (b) Collman, J. P.; Zhang, X.; Lee, V. J.; Uffelman, E. S.; Brauman, J. I. Science 1993, 261, 1404-1411. (c) Allain, E. J.; Hager, L. P.; Deng, L.; Jacobsen, E. N. J. Am. Chem. Soc. 1993, 115, 4415-4416. (d) Brandes, B. D.; Jacobsen, E. N. J. Org. Chem. 1994, 59, 4378-4380. (e) Hosoya, N.; Hatayama, A.; Irie, R.; Sasaki, H.; Katsuki, T. Tetrahedron 1994, 50, 4311-4322. (f) Fukuda, T.; Irie, R.; Katsuki, T. Synlett 1995, 197-198. (g) Collman, J. P.; Lee, V. J.; Kellen-Yuen, C. J.; Zhang, X.; Ibers, J.A.; Brauman, J. I. J. Am. Chem. Soc. 1995, 117, 692-703. (h) Fukuda, T.; Katsuki, T. Tetrahedron Lett. 1996, 37, 4389-4392. (i) Mukaiyama T. Aldrichim. Acta 1996, 29, 59-76.
- (1993) Science , vol.261 , pp. 1404-1411
- Collman, J.P.¹ Zhang, X.² Lee, V.J.³ Uffelman, E.S.⁴ Brauman, J.I.⁵

4
- 9344259269
- For more recent leading references, see: (a) Jacobsen, E. N. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: New York, 1993; Chapter 4.2. (b) Collman, J. P.; Zhang, X.; Lee, V. J.; Uffelman, E. S.; Brauman, J. I. Science 1993, 261, 1404-1411. (c) Allain, E. J.; Hager, L. P.; Deng, L.; Jacobsen, E. N. J. Am. Chem. Soc. 1993, 115, 4415-4416. (d) Brandes, B. D.; Jacobsen, E. N. J. Org. Chem. 1994, 59, 4378-4380. (e) Hosoya, N.; Hatayama, A.; Irie, R.; Sasaki, H.; Katsuki, T. Tetrahedron 1994, 50, 4311-4322. (f) Fukuda, T.; Irie, R.; Katsuki, T. Synlett 1995, 197-198. (g) Collman, J. P.; Lee, V. J.; Kellen-Yuen, C. J.; Zhang, X.; Ibers, J.A.; Brauman, J. I. J. Am. Chem. Soc. 1995, 117, 692-703. (h) Fukuda, T.; Katsuki, T. Tetrahedron Lett. 1996, 37, 4389-4392. (i) Mukaiyama T. Aldrichim. Acta 1996, 29, 59-76.
- (1993) J. Am. Chem. Soc. , vol.115 , pp. 4415-4416
- Allain, E.J.¹ Hager, L.P.² Deng, L.³ Jacobsen, E.N.⁴

5
- 0343597826
- For more recent leading references, see: (a) Jacobsen, E. N. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: New York, 1993; Chapter 4.2. (b) Collman, J. P.; Zhang, X.; Lee, V. J.; Uffelman, E. S.; Brauman, J. I. Science 1993, 261, 1404-1411. (c) Allain, E. J.; Hager, L. P.; Deng, L.; Jacobsen, E. N. J. Am. Chem. Soc. 1993, 115, 4415-4416. (d) Brandes, B. D.; Jacobsen, E. N. J. Org. Chem. 1994, 59, 4378-4380. (e) Hosoya, N.; Hatayama, A.; Irie, R.; Sasaki, H.; Katsuki, T. Tetrahedron 1994, 50, 4311-4322. (f) Fukuda, T.; Irie, R.; Katsuki, T. Synlett 1995, 197-198. (g) Collman, J. P.; Lee, V. J.; Kellen-Yuen, C. J.; Zhang, X.; Ibers, J.A.; Brauman, J. I. J. Am. Chem. Soc. 1995, 117, 692-703. (h) Fukuda, T.; Katsuki, T. Tetrahedron Lett. 1996, 37, 4389-4392. (i) Mukaiyama T. Aldrichim. Acta 1996, 29, 59-76.
- (1994) J. Org. Chem. , vol.59 , pp. 4378-4380
- Brandes, B.D.¹ Jacobsen, E.N.²

6
- 0028356107
- For more recent leading references, see: (a) Jacobsen, E. N. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: New York, 1993; Chapter 4.2. (b) Collman, J. P.; Zhang, X.; Lee, V. J.; Uffelman, E. S.; Brauman, J. I. Science 1993, 261, 1404-1411. (c) Allain, E. J.; Hager, L. P.; Deng, L.; Jacobsen, E. N. J. Am. Chem. Soc. 1993, 115, 4415-4416. (d) Brandes, B. D.; Jacobsen, E. N. J. Org. Chem. 1994, 59, 4378-4380. (e) Hosoya, N.; Hatayama, A.; Irie, R.; Sasaki, H.; Katsuki, T. Tetrahedron 1994, 50, 4311-4322. (f) Fukuda, T.; Irie, R.; Katsuki, T. Synlett 1995, 197-198. (g) Collman, J. P.; Lee, V. J.; Kellen-Yuen, C. J.; Zhang, X.; Ibers, J.A.; Brauman, J. I. J. Am. Chem. Soc. 1995, 117, 692-703. (h) Fukuda, T.; Katsuki, T. Tetrahedron Lett. 1996, 37, 4389-4392. (i) Mukaiyama T. Aldrichim. Acta 1996, 29, 59-76.
- (1994) Tetrahedron , vol.50 , pp. 4311-4322
- Hosoya, N.¹ Hatayama, A.² Irie, R.³ Sasaki, H.⁴ Katsuki, T.⁵

7
- 85064629737
- For more recent leading references, see: (a) Jacobsen, E. N. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: New York, 1993; Chapter 4.2. (b) Collman, J. P.; Zhang, X.; Lee, V. J.; Uffelman, E. S.; Brauman, J. I. Science 1993, 261, 1404-1411. (c) Allain, E. J.; Hager, L. P.; Deng, L.; Jacobsen, E. N. J. Am. Chem. Soc. 1993, 115, 4415-4416. (d) Brandes, B. D.; Jacobsen, E. N. J. Org. Chem. 1994, 59, 4378-4380. (e) Hosoya, N.; Hatayama, A.; Irie, R.; Sasaki, H.; Katsuki, T. Tetrahedron 1994, 50, 4311-4322. (f) Fukuda, T.; Irie, R.; Katsuki, T. Synlett 1995, 197-198. (g) Collman, J. P.; Lee, V. J.; Kellen-Yuen, C. J.; Zhang, X.; Ibers, J.A.; Brauman, J. I. J. Am. Chem. Soc. 1995, 117, 692-703. (h) Fukuda, T.; Katsuki, T. Tetrahedron Lett. 1996, 37, 4389-4392. (i) Mukaiyama T. Aldrichim. Acta 1996, 29, 59-76.
- (1995) Synlett , pp. 197-198
- Fukuda, T.¹ Irie, R.² Katsuki, T.³

8
- 0344723957
- For more recent leading references, see: (a) Jacobsen, E. N. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: New York, 1993; Chapter 4.2. (b) Collman, J. P.; Zhang, X.; Lee, V. J.; Uffelman, E. S.; Brauman, J. I. Science 1993, 261, 1404-1411. (c) Allain, E. J.; Hager, L. P.; Deng, L.; Jacobsen, E. N. J. Am. Chem. Soc. 1993, 115, 4415-4416. (d) Brandes, B. D.; Jacobsen, E. N. J. Org. Chem. 1994, 59, 4378-4380. (e) Hosoya, N.; Hatayama, A.; Irie, R.; Sasaki, H.; Katsuki, T. Tetrahedron 1994, 50, 4311-4322. (f) Fukuda, T.; Irie, R.; Katsuki, T. Synlett 1995, 197-198. (g) Collman, J. P.; Lee, V. J.; Kellen-Yuen, C. J.; Zhang, X.; Ibers, J.A.; Brauman, J. I. J. Am. Chem. Soc. 1995, 117, 692-703. (h) Fukuda, T.; Katsuki, T. Tetrahedron Lett. 1996, 37, 4389-4392. (i) Mukaiyama T. Aldrichim. Acta 1996, 29, 59-76.
- (1995) J. Am. Chem. Soc. , vol.117 , pp. 692-703
- Collman, J.P.¹ Lee, V.J.² Kellen-Yuen, C.J.³ Zhang, X.⁴ Ibers, J.A.⁵ Brauman, J.I.⁶

9
- 0029884163
- For more recent leading references, see: (a) Jacobsen, E. N. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: New York, 1993; Chapter 4.2. (b) Collman, J. P.; Zhang, X.; Lee, V. J.; Uffelman, E. S.; Brauman, J. I. Science 1993, 261, 1404-1411. (c) Allain, E. J.; Hager, L. P.; Deng, L.; Jacobsen, E. N. J. Am. Chem. Soc. 1993, 115, 4415-4416. (d) Brandes, B. D.; Jacobsen, E. N. J. Org. Chem. 1994, 59, 4378-4380. (e) Hosoya, N.; Hatayama, A.; Irie, R.; Sasaki, H.; Katsuki, T. Tetrahedron 1994, 50, 4311-4322. (f) Fukuda, T.; Irie, R.; Katsuki, T. Synlett 1995, 197-198. (g) Collman, J. P.; Lee, V. J.; Kellen-Yuen, C. J.; Zhang, X.; Ibers, J.A.; Brauman, J. I. J. Am. Chem. Soc. 1995, 117, 692-703. (h) Fukuda, T.; Katsuki, T. Tetrahedron Lett. 1996, 37, 4389-4392. (i) Mukaiyama T. Aldrichim. Acta 1996, 29, 59-76.
- (1996) Tetrahedron Lett. , vol.37 , pp. 4389-4392
- Fukuda, T.¹ Katsuki, T.²

10
- 0030445798
- For more recent leading references, see: (a) Jacobsen, E. N. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: New York, 1993; Chapter 4.2. (b) Collman, J. P.; Zhang, X.; Lee, V. J.; Uffelman, E. S.; Brauman, J. I. Science 1993, 261, 1404-1411. (c) Allain, E. J.; Hager, L. P.; Deng, L.; Jacobsen, E. N. J. Am. Chem. Soc. 1993, 115, 4415-4416. (d) Brandes, B. D.; Jacobsen, E. N. J. Org. Chem. 1994, 59, 4378-4380. (e) Hosoya, N.; Hatayama, A.; Irie, R.; Sasaki, H.; Katsuki, T. Tetrahedron 1994, 50, 4311-4322. (f) Fukuda, T.; Irie, R.; Katsuki, T. Synlett 1995, 197-198. (g) Collman, J. P.; Lee, V. J.; Kellen-Yuen, C. J.; Zhang, X.; Ibers, J.A.; Brauman, J. I. J. Am. Chem. Soc. 1995, 117, 692-703. (h) Fukuda, T.; Katsuki, T. Tetrahedron Lett. 1996, 37, 4389-4392. (i) Mukaiyama T. Aldrichim. Acta 1996, 29, 59-76.
- (1996) Aldrichim. Acta , vol.29 , pp. 59-76
- Mukaiyama, T.¹

11
- 0024826999
- (3) For additional leading references on the asymmetric epoxidation of unfunctionalized olefins, see: (a) O'Malley, S.; Kodadek, T. J. Am. Chem. Soc. 1989, 111, 9116-9117. (b) Groves, J. T.; Viski, P. J. Org. Chem. 1990, 55, 3628-3634. (c) Naruta, Y.; Tani, F.; Ishihara, N.; Maruyama, K. J. Am. Chem. Soc. 1991, 113, 6865-6872. (d) Halterman, R. L.; Jan, S.-T. J. Org. Chem. 1991, 56, 5253-5254. (e) O'Connor, K. J.; Wey, S-J.; Burrows, C. J. Tetrahedron Lett. 1992, 33, 1001-1004.
- (1989) J. Am. Chem. Soc. , vol.111 , pp. 9116-9117
- O'Malley, S.¹ Kodadek, T.²

12
- 0007894254
- For additional leading references on the asymmetric epoxidation of unfunctionalized olefins, see: (a) O'Malley, S.; Kodadek, T. J. Am. Chem. Soc. 1989, 111, 9116-9117. (b) Groves, J. T.; Viski, P. J. Org. Chem. 1990, 55, 3628-3634. (c) Naruta, Y.; Tani, F.; Ishihara, N.; Maruyama, K. J. Am. Chem. Soc. 1991, 113, 6865-6872. (d) Halterman, R. L.; Jan, S.-T. J. Org. Chem. 1991, 56, 5253-5254. (e) O'Connor, K. J.; Wey, S-J.; Burrows, C. J. Tetrahedron Lett. 1992, 33, 1001-1004.
- (1990) J. Org. Chem. , vol.55 , pp. 3628-3634
- Groves, J.T.¹ Viski, P.²

13
- 84956418279
- For additional leading references on the asymmetric epoxidation of unfunctionalized olefins, see: (a) O'Malley, S.; Kodadek, T. J. Am. Chem. Soc. 1989, 111, 9116-9117. (b) Groves, J. T.; Viski, P. J. Org. Chem. 1990, 55, 3628-3634. (c) Naruta, Y.; Tani, F.; Ishihara, N.; Maruyama, K. J. Am. Chem. Soc. 1991, 113, 6865-6872. (d) Halterman, R. L.; Jan, S.-T. J. Org. Chem. 1991, 56, 5253-5254. (e) O'Connor, K. J.; Wey, S-J.; Burrows, C. J. Tetrahedron Lett. 1992, 33, 1001-1004.
- (1991) J. Am. Chem. Soc. , vol.113 , pp. 6865-6872
- Naruta, Y.¹ Tani, F.² Ishihara, N.³ Maruyama, K.⁴

14
- 33751499074
- For additional leading references on the asymmetric epoxidation of unfunctionalized olefins, see: (a) O'Malley, S.; Kodadek, T. J. Am. Chem. Soc. 1989, 111, 9116-9117. (b) Groves, J. T.; Viski, P. J. Org. Chem. 1990, 55, 3628-3634. (c) Naruta, Y.; Tani, F.; Ishihara, N.; Maruyama, K. J. Am. Chem. Soc. 1991, 113, 6865-6872. (d) Halterman, R. L.; Jan, S.-T. J. Org. Chem. 1991, 56, 5253-5254. (e) O'Connor, K. J.; Wey, S-J.; Burrows, C. J. Tetrahedron Lett. 1992, 33, 1001-1004.
- (1991) J. Org. Chem. , vol.56 , pp. 5253-5254
- Halterman, R.L.¹ Jan, S.-T.²

15
- 0026520295
- For additional leading references on the asymmetric epoxidation of unfunctionalized olefins, see: (a) O'Malley, S.; Kodadek, T. J. Am. Chem. Soc. 1989, 111, 9116-9117. (b) Groves, J. T.; Viski, P. J. Org. Chem. 1990, 55, 3628-3634. (c) Naruta, Y.; Tani, F.; Ishihara, N.; Maruyama, K. J. Am. Chem. Soc. 1991, 113, 6865-6872. (d) Halterman, R. L.; Jan, S.-T. J. Org. Chem. 1991, 56, 5253-5254. (e) O'Connor, K. J.; Wey, S-J.; Burrows, C. J. Tetrahedron Lett. 1992, 33, 1001-1004.
- (1992) Tetrahedron Lett. , vol.33 , pp. 1001-1004
- O'Connor, K.J.¹ Wey, S.-J.² Burrows, C.J.³

16
- 0000662746
- (a) Chang, S.; Galvin, J. M.; Jacobsen, E. N. J. Am. Chem. Soc. 1994, 116, 6937-6938.
- (1994) J. Am. Chem. Soc. , vol.116 , pp. 6937-6938
- Chang, S.¹ Galvin, J.M.² Jacobsen, E.N.³

17
- 1842383416
- Reference 2d
- (b) Reference 2d.

18
- 0028863959
- and references cited therein
- (c) Bousquet, C.; Gilheany, D. G. Tetrahedron Lett. 1995, 36, 7739-7742 and references cited therein.
- (1995) Tetrahedron Lett. , vol.36 , pp. 7739-7742
- Bousquet, C.¹ Gilheany, D.G.²

19
- 0001121544
- (5) For reviews, see: (a) Rebek, J., Jr. Heterocycles 1981, 15, 517-545. (b) Davis, F. A.; Chen, B. C. Chem. Rev. 1992, 92, 919-934. (c) Besse, P.; Veschambre, H. Tetrahedron 1994, 50, 8885-8927.
- (1981) Heterocycles , vol.15 , pp. 517-545
- Rebek Jr., J.¹

20
- 0000043848
- (5) For reviews, see: (a) Rebek, J., Jr. Heterocycles 1981, 15, 517-545. (b) Davis, F. A.; Chen, B. C. Chem. Rev. 1992, 92, 919-934. (c) Besse, P.; Veschambre, H. Tetrahedron 1994, 50, 8885-8927.
- (1992) Chem. Rev. , vol.92 , pp. 919-934
- Davis, F.A.¹ Chen, B.C.²

21
- 0027934450
- (5) For reviews, see: (a) Rebek, J., Jr. Heterocycles 1981, 15, 517-545. (b) Davis, F. A.; Chen, B. C. Chem. Rev. 1992, 92, 919-934. (c) Besse, P.; Veschambre, H. Tetrahedron 1994, 50, 8885-8927.
- (1994) Tetrahedron , vol.50 , pp. 8885-8927
- Besse, P.¹ Veschambre, H.²

22
- 0000276826
- (6) For recent leading references, see: (a) Koch, A.; Reymond, J.-L.; Lerner, R. A. J. Am. Chem. Soc. 1994, 116, 803-804. (b) Aggarwal, V. K.; Wang, M. F. J. Chem. Soc., Chem. Commun. 1996, 191-192. (c) Li, A.-H.; Dai, L.-X.; Hou. X.-L.; Huang, Y.-Z.; Li, F.-W. J. Org. Chem. 1996, 61, 489-493. (d) Aggarwal, V. K.; Ford, J. G.; Thompson, A.; Jones, R. V. H.; Standen, M. C. H. J. Am. Chem. Soc. 1996, 118, 7004-7005. (e) Enders, D.; Zhu, J.; Raabe, G. Angew. Chem., Int. Ed. Engl. 1996, 35, 1725-1728. (f) Elston, C. L.; Jackson, R. F. W.; MacDonald, S. J. F.; Murray, P. J. Angew. Chem., Int. Ed. Engl. 1997, 36, 410-412. (g) Bougauchi, M.; Watanabe, S.; Arai, T.; Sasai, H.; Shibasaki, M. J. Am. Chem. Soc. 1997, 119, 2329-2330. (h) Bentley, P. A.; Bergeron, S.; Cappi, M. W.; Hibbs, D. E.; Hursthouse, M. B.; Nugent, T. C.; Pulido, R.; Roberts, S. M.; Wu, L. E. J. Chem. Soc., Chem. Commun. 1997, 739-740.
- (1994) J. Am. Chem. Soc. , vol.116 , pp. 803-804
- Koch, A.¹ Reymond, J.-L.² Lerner, R.A.³

23
- 0002499775
- For recent leading references, see: (a) Koch, A.; Reymond, J.-L.; Lerner, R. A. J. Am. Chem. Soc. 1994, 116, 803-804. (b) Aggarwal, V. K.; Wang, M. F. J. Chem. Soc., Chem. Commun. 1996, 191-192. (c) Li, A.-H.; Dai, L.-X.; Hou. X.-L.; Huang, Y.-Z.; Li, F.-W. J. Org. Chem. 1996, 61, 489-493. (d) Aggarwal, V. K.; Ford, J. G.; Thompson, A.; Jones, R. V. H.; Standen, M. C. H. J. Am. Chem. Soc. 1996, 118, 7004-7005. (e) Enders, D.; Zhu, J.; Raabe, G. Angew. Chem., Int. Ed. Engl. 1996, 35, 1725-1728. (f) Elston, C. L.; Jackson, R. F. W.; MacDonald, S. J. F.; Murray, P. J. Angew. Chem., Int. Ed. Engl. 1997, 36, 410-412. (g) Bougauchi, M.; Watanabe, S.; Arai, T.; Sasai, H.; Shibasaki, M. J. Am. Chem. Soc. 1997, 119, 2329-2330. (h) Bentley, P. A.; Bergeron, S.; Cappi, M. W.; Hibbs, D. E.; Hursthouse, M. B.; Nugent, T. C.; Pulido, R.; Roberts, S. M.; Wu, L. E. J. Chem. Soc., Chem. Commun. 1997, 739-740.
- (1996) J. Chem. Soc., Chem. Commun. , pp. 191-192
- Aggarwal, V.K.¹ Wang, M.F.²

24
- 0030024622
- For recent leading references, see: (a) Koch, A.; Reymond, J.-L.; Lerner, R. A. J. Am. Chem. Soc. 1994, 116, 803-804. (b) Aggarwal, V. K.; Wang, M. F. J. Chem. Soc., Chem. Commun. 1996, 191-192. (c) Li, A.-H.; Dai, L.-X.; Hou. X.-L.; Huang, Y.-Z.; Li, F.-W. J. Org. Chem. 1996, 61, 489-493. (d) Aggarwal, V. K.; Ford, J. G.; Thompson, A.; Jones, R. V. H.; Standen, M. C. H. J. Am. Chem. Soc. 1996, 118, 7004-7005. (e) Enders, D.; Zhu, J.; Raabe, G. Angew. Chem., Int. Ed. Engl. 1996, 35, 1725-1728. (f) Elston, C. L.; Jackson, R. F. W.; MacDonald, S. J. F.; Murray, P. J. Angew. Chem., Int. Ed. Engl. 1997, 36, 410-412. (g) Bougauchi, M.; Watanabe, S.; Arai, T.; Sasai, H.; Shibasaki, M. J. Am. Chem. Soc. 1997, 119, 2329-2330. (h) Bentley, P. A.; Bergeron, S.; Cappi, M. W.; Hibbs, D. E.; Hursthouse, M. B.; Nugent, T. C.; Pulido, R.; Roberts, S. M.; Wu, L. E. J. Chem. Soc., Chem. Commun. 1997, 739-740.
- (1996) J. Org. Chem. , vol.61 , pp. 489-493
- Li, A.-H.¹ Dai, L.-X.² Hou, X.-L.³ Huang, Y.-Z.⁴ Li, F.-W.⁵

25
- 0029900606
- For recent leading references, see: (a) Koch, A.; Reymond, J.-L.; Lerner, R. A. J. Am. Chem. Soc. 1994, 116, 803-804. (b) Aggarwal, V. K.; Wang, M. F. J. Chem. Soc., Chem. Commun. 1996, 191-192. (c) Li, A.-H.; Dai, L.-X.; Hou. X.-L.; Huang, Y.-Z.; Li, F.-W. J. Org. Chem. 1996, 61, 489-493. (d) Aggarwal, V. K.; Ford, J. G.; Thompson, A.; Jones, R. V. H.; Standen, M. C. H. J. Am. Chem. Soc. 1996, 118, 7004-7005. (e) Enders, D.; Zhu, J.; Raabe, G. Angew. Chem., Int. Ed. Engl. 1996, 35, 1725-1728. (f) Elston, C. L.; Jackson, R. F. W.; MacDonald, S. J. F.; Murray, P. J. Angew. Chem., Int. Ed. Engl. 1997, 36, 410-412. (g) Bougauchi, M.; Watanabe, S.; Arai, T.; Sasai, H.; Shibasaki, M. J. Am. Chem. Soc. 1997, 119, 2329-2330. (h) Bentley, P. A.; Bergeron, S.; Cappi, M. W.; Hibbs, D. E.; Hursthouse, M. B.; Nugent, T. C.; Pulido, R.; Roberts, S. M.; Wu, L. E. J. Chem. Soc., Chem. Commun. 1997, 739-740.
- (1996) J. Am. Chem. Soc. , vol.118 , pp. 7004-7005
- Aggarwal, V.K.¹ Ford, J.G.² Thompson, A.³ Jones, R.V.H.⁴ Standen, M.C.H.⁵

26
- 0029785064
- For recent leading references, see: (a) Koch, A.; Reymond, J.-L.; Lerner, R. A. J. Am. Chem. Soc. 1994, 116, 803-804. (b) Aggarwal, V. K.; Wang, M. F. J. Chem. Soc., Chem. Commun. 1996, 191-192. (c) Li, A.-H.; Dai, L.-X.; Hou. X.-L.; Huang, Y.-Z.; Li, F.-W. J. Org. Chem. 1996, 61, 489-493. (d) Aggarwal, V. K.; Ford, J. G.; Thompson, A.; Jones, R. V. H.; Standen, M. C. H. J. Am. Chem. Soc. 1996, 118, 7004-7005. (e) Enders, D.; Zhu, J.; Raabe, G. Angew. Chem., Int. Ed. Engl. 1996, 35, 1725-1728. (f) Elston, C. L.; Jackson, R. F. W.; MacDonald, S. J. F.; Murray, P. J. Angew. Chem., Int. Ed. Engl. 1997, 36, 410-412. (g) Bougauchi, M.; Watanabe, S.; Arai, T.; Sasai, H.; Shibasaki, M. J. Am. Chem. Soc. 1997, 119, 2329-2330. (h) Bentley, P. A.; Bergeron, S.; Cappi, M. W.; Hibbs, D. E.; Hursthouse, M. B.; Nugent, T. C.; Pulido, R.; Roberts, S. M.; Wu, L. E. J. Chem. Soc., Chem. Commun. 1997, 739-740.
- (1996) Angew. Chem., Int. Ed. Engl. , vol.35 , pp. 1725-1728
- Enders, D.¹ Zhu, J.² Raabe, G.³

27
- 0030895780
- For recent leading references, see: (a) Koch, A.; Reymond, J.-L.; Lerner, R. A. J. Am. Chem. Soc. 1994, 116, 803-804. (b) Aggarwal, V. K.; Wang, M. F. J. Chem. Soc., Chem. Commun. 1996, 191-192. (c) Li, A.-H.; Dai, L.-X.; Hou. X.-L.; Huang, Y.-Z.; Li, F.-W. J. Org. Chem. 1996, 61, 489-493. (d) Aggarwal, V. K.; Ford, J. G.; Thompson, A.; Jones, R. V. H.; Standen, M. C. H. J. Am. Chem. Soc. 1996, 118, 7004-7005. (e) Enders, D.; Zhu, J.; Raabe, G. Angew. Chem., Int. Ed. Engl. 1996, 35, 1725-1728. (f) Elston, C. L.; Jackson, R. F. W.; MacDonald, S. J. F.; Murray, P. J. Angew. Chem., Int. Ed. Engl. 1997, 36, 410-412. (g) Bougauchi, M.; Watanabe, S.; Arai, T.; Sasai, H.; Shibasaki, M. J. Am. Chem. Soc. 1997, 119, 2329-2330. (h) Bentley, P. A.; Bergeron, S.; Cappi, M. W.; Hibbs, D. E.; Hursthouse, M. B.; Nugent, T. C.; Pulido, R.; Roberts, S. M.; Wu, L. E. J. Chem. Soc., Chem. Commun. 1997, 739-740.
- (1997) Angew. Chem., Int. Ed. Engl. , vol.36 , pp. 410-412
- Elston, C.L.¹ Jackson, R.F.W.² MacDonald, S.J.F.³ Murray, P.J.⁴

28
- 0030964434
- For recent leading references, see: (a) Koch, A.; Reymond, J.-L.; Lerner, R. A. J. Am. Chem. Soc. 1994, 116, 803-804. (b) Aggarwal, V. K.; Wang, M. F. J. Chem. Soc., Chem. Commun. 1996, 191-192. (c) Li, A.-H.; Dai, L.-X.; Hou. X.-L.; Huang, Y.-Z.; Li, F.-W. J. Org. Chem. 1996, 61, 489-493. (d) Aggarwal, V. K.; Ford, J. G.; Thompson, A.; Jones, R. V. H.; Standen, M. C. H. J. Am. Chem. Soc. 1996, 118, 7004-7005. (e) Enders, D.; Zhu, J.; Raabe, G. Angew. Chem., Int. Ed. Engl. 1996, 35, 1725-1728. (f) Elston, C. L.; Jackson, R. F. W.; MacDonald, S. J. F.; Murray, P. J. Angew. Chem., Int. Ed. Engl. 1997, 36, 410-412. (g) Bougauchi, M.; Watanabe, S.; Arai, T.; Sasai, H.; Shibasaki, M. J. Am. Chem. Soc. 1997, 119, 2329-2330. (h) Bentley, P. A.; Bergeron, S.; Cappi, M. W.; Hibbs, D. E.; Hursthouse, M. B.; Nugent, T. C.; Pulido, R.; Roberts, S. M.; Wu, L. E. J. Chem. Soc., Chem. Commun. 1997, 739-740.
- (1997) J. Am. Chem. Soc. , vol.119 , pp. 2329-2330
- Bougauchi, M.¹ Watanabe, S.² Arai, T.³ Sasai, H.⁴ Shibasaki, M.⁵

29
- 0002820846
- For recent leading references, see: (a) Koch, A.; Reymond, J.-L.; Lerner, R. A. J. Am. Chem. Soc. 1994, 116, 803-804. (b) Aggarwal, V. K.; Wang, M. F. J. Chem. Soc., Chem. Commun. 1996, 191-192. (c) Li, A.-H.; Dai, L.-X.; Hou. X.-L.; Huang, Y.-Z.; Li, F.-W. J. Org. Chem. 1996, 61, 489-493. (d) Aggarwal, V. K.; Ford, J. G.; Thompson, A.; Jones, R. V. H.; Standen, M. C. H. J. Am. Chem. Soc. 1996, 118, 7004-7005. (e) Enders, D.; Zhu, J.; Raabe, G. Angew. Chem., Int. Ed. Engl. 1996, 35, 1725-1728. (f) Elston, C. L.; Jackson, R. F. W.; MacDonald, S. J. F.; Murray, P. J. Angew. Chem., Int. Ed. Engl. 1997, 36, 410-412. (g) Bougauchi, M.; Watanabe, S.; Arai, T.; Sasai, H.; Shibasaki, M. J. Am. Chem. Soc. 1997, 119, 2329-2330. (h) Bentley, P. A.; Bergeron, S.; Cappi, M. W.; Hibbs, D. E.; Hursthouse, M. B.; Nugent, T. C.; Pulido, R.; Roberts, S. M.; Wu, L. E. J. Chem. Soc., Chem. Commun. 1997, 739-740.
- (1997) J. Chem. Soc., Chem. Commun. , pp. 739-740
- Bentley, P.A.¹ Bergeron, S.² Cappi, M.W.³ Hibbs, D.E.⁴ Hursthouse, M.B.⁵ Nugent, T.C.⁶ Pulido, R.⁷ Roberts, S.M.⁸ Wu, L.E.⁹

30
- 0001742543
- For general leading references on dioxiranes, see: (a) Adam, W.; Curci, R.; Edwards, J. O. Acc. Chem. Res. 1989, 22, 205-211. (b) Murray, R. W. Chem. Rev. 1989, 89, 1187-1201. (c) Curci, R.; Dinoi, A.; Rubino, M. F. Pure Appl. Chem. 1995, 67, 811-822. (d) Adam, W.; Smerz, A. K. Bull. Soc. Chim. Belg. 1996, 105, 581-599.
- (1989) Acc. Chem. Res. , vol.22 , pp. 205-211
- Adam, W.¹ Curci, R.² Edwards, J.O.³

31
- 6044269298
- For general leading references on dioxiranes, see: (a) Adam, W.; Curci, R.; Edwards, J. O. Acc. Chem. Res. 1989, 22, 205-211. (b) Murray, R. W. Chem. Rev. 1989, 89, 1187-1201. (c) Curci, R.; Dinoi, A.; Rubino, M. F. Pure Appl. Chem. 1995, 67, 811-822. (d) Adam, W.; Smerz, A. K. Bull. Soc. Chim. Belg. 1996, 105, 581-599.
- (1989) Chem. Rev. , vol.89 , pp. 1187-1201
- Murray, R.W.¹

32
- 84948351019
- For general leading references on dioxiranes, see: (a) Adam, W.; Curci, R.; Edwards, J. O. Acc. Chem. Res. 1989, 22, 205-211. (b) Murray, R. W. Chem. Rev. 1989, 89, 1187-1201. (c) Curci, R.; Dinoi, A.; Rubino, M. F. Pure Appl. Chem. 1995, 67, 811-822. (d) Adam, W.; Smerz, A. K. Bull. Soc. Chim. Belg. 1996, 105, 581-599.
- (1995) Pure Appl. Chem. , vol.67 , pp. 811-822
- Curci, R.¹ Dinoi, A.² Rubino, M.F.³

33
- 0001742543
- For general leading references on dioxiranes, see: (a) Adam, W.; Curci, R.; Edwards, J. O. Acc. Chem. Res. 1989, 22, 205-211. (b) Murray, R. W. Chem. Rev. 1989, 89, 1187-1201. (c) Curci, R.; Dinoi, A.; Rubino, M. F. Pure Appl. Chem. 1995, 67, 811-822. (d) Adam, W.; Smerz, A. K. Bull. Soc. Chim. Belg. 1996, 105, 581-599.
- (1996) Bull. Soc. Chim. Belg. , vol.105 , pp. 581-599
- Adam, W.¹ Smerz, A.K.²

34
- 27844577489
- (8) For examples of in situ generation of dioxiranes, see: (a) Edwards, J. O.; Pater, R. H.; Curci, R.; Di Furia, F. Photochem. Photobiol. 1979, 30, 63-70. (b) Curci, R.; Fiorentino, M.; Troisi, L.; Edwards, J. O.; Pater, R. H. J. Org. Chem. 1980, 45, 4758-4760. (c) Gallopo, A. R.; Edwards J. O. J. Org. Chem. 1981, 46, 1684-1688. (d) Cicala, G.; Curci, R.; Fiorentino, M.; Laricchiuta, O. J. Org. Chem. 1982, 47, 2670-2673. (e) Corey, P. F.; Ward, F. E. J. Org. Chem. 1986, 51, 1925-1926. (f) Yang, D.; Wong, M. K.; Yip, Y. C. J. Org. Chem. 1995, 60, 3887-3889 and references cited therein. (g) Denmark, S. E.; Forbes, D. C.; Hays, D. S.; DePue, J. S.; Wilde, R. G. J. Org. Chem. 1995, 60, 1391-1407 and references cited therein.
- (1979) Photochem. Photobiol. , vol.30 , pp. 63-70
- Edwards, J.O.¹ Pater, R.H.² Curci, R.³ Di Furia, F.⁴

35
- 24044469796
- For examples of in situ generation of dioxiranes, see: (a) Edwards, J. O.; Pater, R. H.; Curci, R.; Di Furia, F. Photochem. Photobiol. 1979, 30, 63-70. (b) Curci, R.; Fiorentino, M.; Troisi, L.; Edwards, J. O.; Pater, R. H. J. Org. Chem. 1980, 45, 4758-4760. (c) Gallopo, A. R.; Edwards J. O. J. Org. Chem. 1981, 46, 1684-1688. (d) Cicala, G.; Curci, R.; Fiorentino, M.; Laricchiuta, O. J. Org. Chem. 1982, 47, 2670-2673. (e) Corey, P. F.; Ward, F. E. J. Org. Chem. 1986, 51, 1925-1926. (f) Yang, D.; Wong, M. K.; Yip, Y. C. J. Org. Chem. 1995, 60, 3887-3889 and references cited therein. (g) Denmark, S. E.; Forbes, D. C.; Hays, D. S.; DePue, J. S.; Wilde, R. G. J. Org. Chem. 1995, 60, 1391-1407 and references cited therein.
- (1980) J. Org. Chem. , vol.45 , pp. 4758-4760
- Curci, R.¹ Fiorentino, M.² Troisi, L.³ Edwards, J.O.⁴ Pater, R.H.⁵

36
- 33845556406
- For examples of in situ generation of dioxiranes, see: (a) Edwards, J. O.; Pater, R. H.; Curci, R.; Di Furia, F. Photochem. Photobiol. 1979, 30, 63-70. (b) Curci, R.; Fiorentino, M.; Troisi, L.; Edwards, J. O.; Pater, R. H. J. Org. Chem. 1980, 45, 4758-4760. (c) Gallopo, A. R.; Edwards J. O. J. Org. Chem. 1981, 46, 1684-1688. (d) Cicala, G.; Curci, R.; Fiorentino, M.; Laricchiuta, O. J. Org. Chem. 1982, 47, 2670-2673. (e) Corey, P. F.; Ward, F. E. J. Org. Chem. 1986, 51, 1925-1926. (f) Yang, D.; Wong, M. K.; Yip, Y. C. J. Org. Chem. 1995, 60, 3887-3889 and references cited therein. (g) Denmark, S. E.; Forbes, D. C.; Hays, D. S.; DePue, J. S.; Wilde, R. G. J. Org. Chem. 1995, 60, 1391-1407 and references cited therein.
- (1981) J. Org. Chem. , vol.46 , pp. 1684-1688
- Gallopo, A.R.¹ Edwards, J.O.²

37
- 0001131426
- For examples of in situ generation of dioxiranes, see: (a) Edwards, J. O.; Pater, R. H.; Curci, R.; Di Furia, F. Photochem. Photobiol. 1979, 30, 63-70. (b) Curci, R.; Fiorentino, M.; Troisi, L.; Edwards, J. O.; Pater, R. H. J. Org. Chem. 1980, 45, 4758-4760. (c) Gallopo, A. R.; Edwards J. O. J. Org. Chem. 1981, 46, 1684-1688. (d) Cicala, G.; Curci, R.; Fiorentino, M.; Laricchiuta, O. J. Org. Chem. 1982, 47, 2670-2673. (e) Corey, P. F.; Ward, F. E. J. Org. Chem. 1986, 51, 1925-1926. (f) Yang, D.; Wong, M. K.; Yip, Y. C. J. Org. Chem. 1995, 60, 3887-3889 and references cited therein. (g) Denmark, S. E.; Forbes, D. C.; Hays, D. S.; DePue, J. S.; Wilde, R. G. J. Org. Chem. 1995, 60, 1391-1407 and references cited therein.
- (1982) J. Org. Chem. , vol.47 , pp. 2670-2673
- Cicala, G.¹ Curci, R.² Fiorentino, M.³ Laricchiuta, O.⁴

38
- 33845375878
- For examples of in situ generation of dioxiranes, see: (a) Edwards, J. O.; Pater, R. H.; Curci, R.; Di Furia, F. Photochem. Photobiol. 1979, 30, 63-70. (b) Curci, R.; Fiorentino, M.; Troisi, L.; Edwards, J. O.; Pater, R. H. J. Org. Chem. 1980, 45, 4758-4760. (c) Gallopo, A. R.; Edwards J. O. J. Org. Chem. 1981, 46, 1684-1688. (d) Cicala, G.; Curci, R.; Fiorentino, M.; Laricchiuta, O. J. Org. Chem. 1982, 47, 2670-2673. (e) Corey, P. F.; Ward, F. E. J. Org. Chem. 1986, 51, 1925-1926. (f) Yang, D.; Wong, M. K.; Yip, Y. C. J. Org. Chem. 1995, 60, 3887-3889 and references cited therein. (g) Denmark, S. E.; Forbes, D. C.; Hays, D. S.; DePue, J. S.; Wilde, R. G. J. Org. Chem. 1995, 60, 1391-1407 and references cited therein.
- (1986) J. Org. Chem. , vol.51 , pp. 1925-1926
- Corey, P.F.¹ Ward, F.E.²

39
- 33751154457
- and references cited therein
- For examples of in situ generation of dioxiranes, see: (a) Edwards, J. O.; Pater, R. H.; Curci, R.; Di Furia, F. Photochem. Photobiol. 1979, 30, 63-70. (b) Curci, R.; Fiorentino, M.; Troisi, L.; Edwards, J. O.; Pater, R. H. J. Org. Chem. 1980, 45, 4758-4760. (c) Gallopo, A. R.; Edwards J. O. J. Org. Chem. 1981, 46, 1684-1688. (d) Cicala, G.; Curci, R.; Fiorentino, M.; Laricchiuta, O. J. Org. Chem. 1982, 47, 2670-2673. (e) Corey, P. F.; Ward, F. E. J. Org. Chem. 1986, 51, 1925-1926. (f) Yang, D.; Wong, M. K.; Yip, Y. C. J. Org. Chem. 1995, 60, 3887-3889 and references cited therein. (g) Denmark, S. E.; Forbes, D. C.; Hays, D. S.; DePue, J. S.; Wilde, R. G. J. Org. Chem. 1995, 60, 1391-1407 and references cited therein.
- (1995) J. Org. Chem. , vol.60 , pp. 3887-3889
- Yang, D.¹ Wong, M.K.² Yip, Y.C.³

40
- 0000225906
- and references cited therein
- For examples of in situ generation of dioxiranes, see: (a) Edwards, J. O.; Pater, R. H.; Curci, R.; Di Furia, F. Photochem. Photobiol. 1979, 30, 63-70. (b) Curci, R.; Fiorentino, M.; Troisi, L.; Edwards, J. O.; Pater, R. H. J. Org. Chem. 1980, 45, 4758-4760. (c) Gallopo, A. R.; Edwards J. O. J. Org. Chem. 1981, 46, 1684-1688. (d) Cicala, G.; Curci, R.; Fiorentino, M.; Laricchiuta, O. J. Org. Chem. 1982, 47, 2670-2673. (e) Corey, P. F.; Ward, F. E. J. Org. Chem. 1986, 51, 1925-1926. (f) Yang, D.; Wong, M. K.; Yip, Y. C. J. Org. Chem. 1995, 60, 3887-3889 and references cited therein. (g) Denmark, S. E.; Forbes, D. C.; Hays, D. S.; DePue, J. S.; Wilde, R. G. J. Org. Chem. 1995, 60, 1391-1407 and references cited therein.
- (1995) J. Org. Chem. , vol.60 , pp. 1391-1407
- Denmark, S.E.¹ Forbes, D.C.² Hays, D.S.³ DePue, J.S.⁴ Wilde, R.G.⁵

41
- 37049107720
- (9) For examples of asymmetric epoxidation mediated by chiral ketones, see: (a) Curci, R.; Fiorentino, M.; Serio, M. R. J. Chem. Soc., Chem. Commun. 1984, 155-156. (b) Curci, R.; D'Accolti, L.; Fiorentino, M.; Rosa, A. Tetrahedron Lett. 1995, 36, 5831-5834. (c) Reference 8g. (d) Brown, D. S.; Marples, B. A.; Smith, P.; Walton, L. Tetrahedron 1995, 51, 3587-3606. (e) Yang, D.; Yip, Y. C.; Tang, M. W.; Wong, M. K.; Zheng, J. H.; Cheung, K. K. J. Am. Chem. Soc. 1996, 118, 491-492. (f) Yang, D.; Wang, X.-C.; Wong, M.-K.; Yip, Y.-C.; Tang, M.-W. J. Am. Chem. Soc. 1996, 118, 11311-11312.
- (1984) J. Chem. Soc., Chem. Commun. , pp. 155-156
- Curci, R.¹ Fiorentino, M.² Serio, M.R.³

42
- 0029118915
- For examples of asymmetric epoxidation mediated by chiral ketones, see: (a) Curci, R.; Fiorentino, M.; Serio, M. R. J. Chem. Soc., Chem. Commun. 1984, 155-156. (b) Curci, R.; D'Accolti, L.; Fiorentino, M.; Rosa, A. Tetrahedron Lett. 1995, 36, 5831-5834. (c) Reference 8g. (d) Brown, D. S.; Marples, B. A.; Smith, P.; Walton, L. Tetrahedron 1995, 51, 3587-3606. (e) Yang, D.; Yip, Y. C.; Tang, M. W.; Wong, M. K.; Zheng, J. H.; Cheung, K. K. J. Am. Chem. Soc. 1996, 118, 491-492. (f) Yang, D.; Wang, X.-C.; Wong, M.-K.; Yip, Y.-C.; Tang, M.-W. J. Am. Chem. Soc. 1996, 118, 11311-11312.
- (1995) Tetrahedron Lett. , vol.36 , pp. 5831-5834
- Curci, R.¹ D'Accolti, L.² Fiorentino, M.³ Rosa, A.⁴

43
- 1842340934
- Reference 8g
- For examples of asymmetric epoxidation mediated by chiral ketones, see: (a) Curci, R.; Fiorentino, M.; Serio, M. R. J. Chem. Soc., Chem. Commun. 1984, 155-156. (b) Curci, R.; D'Accolti, L.; Fiorentino, M.; Rosa, A. Tetrahedron Lett. 1995, 36, 5831-5834. (c) Reference 8g. (d) Brown, D. S.; Marples, B. A.; Smith, P.; Walton, L. Tetrahedron 1995, 51, 3587-3606. (e) Yang, D.; Yip, Y. C.; Tang, M. W.; Wong, M. K.; Zheng, J. H.; Cheung, K. K. J. Am. Chem. Soc. 1996, 118, 491-492. (f) Yang, D.; Wang, X.-C.; Wong, M.-K.; Yip, Y.-C.; Tang, M.-W. J. Am. Chem. Soc. 1996, 118, 11311-11312.

44
- 0028937666
- For examples of asymmetric epoxidation mediated by chiral ketones, see: (a) Curci, R.; Fiorentino, M.; Serio, M. R. J. Chem. Soc., Chem. Commun. 1984, 155-156. (b) Curci, R.; D'Accolti, L.; Fiorentino, M.; Rosa, A. Tetrahedron Lett. 1995, 36, 5831-5834. (c) Reference 8g. (d) Brown, D. S.; Marples, B. A.; Smith, P.; Walton, L. Tetrahedron 1995, 51, 3587-3606. (e) Yang, D.; Yip, Y. C.; Tang, M. W.; Wong, M. K.; Zheng, J. H.; Cheung, K. K. J. Am. Chem. Soc. 1996, 118, 491-492. (f) Yang, D.; Wang, X.-C.; Wong, M.-K.; Yip, Y.-C.; Tang, M.-W. J. Am. Chem. Soc. 1996, 118, 11311-11312.
- (1995) Tetrahedron , vol.51 , pp. 3587-3606
- Brown, D.S.¹ Marples, B.A.² Smith, P.³ Walton, L.⁴

45
- 3643086474
- For examples of asymmetric epoxidation mediated by chiral ketones, see: (a) Curci, R.; Fiorentino, M.; Serio, M. R. J. Chem. Soc., Chem. Commun. 1984, 155-156. (b) Curci, R.; D'Accolti, L.; Fiorentino, M.; Rosa, A. Tetrahedron Lett. 1995, 36, 5831-5834. (c) Reference 8g. (d) Brown, D. S.; Marples, B. A.; Smith, P.; Walton, L. Tetrahedron 1995, 51, 3587-3606. (e) Yang, D.; Yip, Y. C.; Tang, M. W.; Wong, M. K.; Zheng, J. H.; Cheung, K. K. J. Am. Chem. Soc. 1996, 118, 491-492. (f) Yang, D.; Wang, X.-C.; Wong, M.-K.; Yip, Y.-C.; Tang, M.-W. J. Am. Chem. Soc. 1996, 118, 11311-11312.
- (1996) J. Am. Chem. Soc. , vol.118 , pp. 491-492
- Yang, D.¹ Yip, Y.C.² Tang, M.W.³ Wong, M.K.⁴ Zheng, J.H.⁵ Cheung, K.K.⁶

46
- 0029923940
- For examples of asymmetric epoxidation mediated by chiral ketones, see: (a) Curci, R.; Fiorentino, M.; Serio, M. R. J. Chem. Soc., Chem. Commun. 1984, 155-156. (b) Curci, R.; D'Accolti, L.; Fiorentino, M.; Rosa, A. Tetrahedron Lett. 1995, 36, 5831-5834. (c) Reference 8g. (d) Brown, D. S.; Marples, B. A.; Smith, P.; Walton, L. Tetrahedron 1995, 51, 3587-3606. (e) Yang, D.; Yip, Y. C.; Tang, M. W.; Wong, M. K.; Zheng, J. H.; Cheung, K. K. J. Am. Chem. Soc. 1996, 118, 491-492. (f) Yang, D.; Wang, X.-C.; Wong, M.-K.; Yip, Y.-C.; Tang, M.-W. J. Am. Chem. Soc. 1996, 118, 11311-11312.
- (1996) J. Am. Chem. Soc. , vol.118 , pp. 11311-11312
- Yang, D.¹ Wang, X.-C.² Wong, M.-K.³ Yip, Y.-C.⁴ Tang, M.-W.⁵

47
- 0029860777
- Tu, Y.; Wang, Z.-X.; Shi, Y. J. Am. Chem. Soc. 1996, 118, 9806-9807.
- (1996) J. Am. Chem. Soc. , vol.118 , pp. 9806-9807
- Tu, Y.¹ Wang, Z.-X.² Shi, Y.³

48
- 0001554971
- Wang, Z.-X.; Tu, Y.; Frohn, M.; Shi, Y. J. Org. Chem. 1997, 62, 2328-2329.
- (1997) J. Org. Chem. , vol.62 , pp. 2328-2329
- Wang, Z.-X.¹ Tu, Y.² Frohn, M.³ Shi, Y.⁴

49
- 0025979778
- Mio, S.; Kumagawa, Y.; Sugai, S. Tetrahedron 1991, 47, 2133-2144.
- (1991) Tetrahedron , vol.47 , pp. 2133-2144
- Mio, S.¹ Kumagawa, Y.² Sugai, S.³

50
- 0000366457
- Chen, C.-C.; Whistler, R. L. Carbohydr. Res. 1988, 175, 265-271.
- (1988) Carbohydr. Res. , vol.175 , pp. 265-271
- Chen, C.-C.¹ Whistler, R.L.²

51
- 1842275746
- note
- Attempts to identify the decomposition products so far have been unsuccessful.

52
- 33947466373
- (a) Ball, D. L.; Edwards, J. O. J. Am. Chem. Soc. 1956, 78, 1125-1129.
- (1956) J. Am. Chem. Soc. , vol.78 , pp. 1125-1129
- Ball, D.L.¹ Edwards, J.O.²

53
- 33847804991
- (b) Montgomery, R. E. J. Am. Chem. Soc. 1974, 96, 7820-7821.
- (1974) J. Am. Chem. Soc. , vol.96 , pp. 7820-7821
- Montgomery, R.E.¹

54
- 0028273577
- Kurihara, M.; Ito, S.; Tsutsumi, N.; Miyata, N. Tetrahedron Lett. 1994, 35, 1577-1580.
- (1994) Tetrahedron Lett. , vol.35 , pp. 1577-1580
- Kurihara, M.¹ Ito, S.² Tsutsumi, N.³ Miyata, N.⁴

55
- 33845556406
- (a) There is a report showing that the catalytic efficiency of cyclohexanone for the oxidation of pyridine with Oxone is maximized at a slightly higher pH (8.5). The data suggest that, at this pH, the Baeyer-Villiger process of cyclohexanone is minimized; see: Gallopo, A. R.; Edwards, J. O. J. Org. Chem. 1981, 46, 1684-1688.
- (1981) J. Org. Chem. , vol.46 , pp. 1684-1688
- Gallopo, A.R.¹ Edwards, J.O.²

56
- 1842390282
- note
- (b) There is also a report suggesting that the Baeyer-Villiger reaction might become significant at high pH values (pH > 11); see ref 8a.

57
- 1842392249
- note
- Under this condition, the epoxidation in the absence of the ketone catalyst is negligible within 2 h reaction time.

58
- 1842380576
- note
- In the literature, a large excess of Oxone (>5 equiv) is often used to achieve good conversions of olefins.

59
- 0000500836
- (a) Baumstark, A. L.; McCloskey, C. J. Tetrahedron Lett. 1987, 28, 3311-3314.
- (1987) J. Tetrahedron Lett. , vol.28 , pp. 3311-3314
- Baumstark, A.L.¹ McCloskey, C.²

60
- 33845280766
- (b) Baumstark, A. L.; Vasquez, P. C. J. Org. Chem. 1988, 53, 3437-3439.
- (1988) J. Org. Chem. , vol.53 , pp. 3437-3439
- Baumstark, A.L.¹ Vasquez, P.C.²

61
- 0001564432
- Bach, R. D.; Andres, J. L.; Owensby, A. L.; Schlegel, H. B.; McDouall, J. J. W. J. Am. Chem. Soc. 1992, 114, 7207-7217.
- (1992) J. Am. Chem. Soc. , vol.114 , pp. 7207-7217
- Bach, R.D.¹ Andres, J.L.² Owensby, A.L.³ Schlegel, H.B.⁴ McDouall, J.J.W.⁵

62
- 0000450582
- (22) It is interesting to note that both experimental and theoretical studies suggested that the epoxidation of olefins with oxaziridine proceeded preferably via a planar transition state: (a) Davis, F. A.; Harakal, M. E.; Awad, S. B. J. Am. Chem. Soc. 1983, 105, 3123-3126. (b) Bach, R. D.; Wolber, G. J. J. Am. Chem. Soc. 1984, 106, 1410-1415. (c) Davis, F. A.; Chattopadhyay, S. Tetrahedron Lett. 1986, 27, 5079-5082.
- (1983) J. Am. Chem. Soc. , vol.105 , pp. 3123-3126
- Davis, F.A.¹ Harakal, M.E.² Awad, S.B.³

63
- 0021756752
- It is interesting to note that both experimental and theoretical studies suggested that the epoxidation of olefins with oxaziridine proceeded preferably via a planar transition state: (a) Davis, F. A.; Harakal, M. E.; Awad, S. B. J. Am. Chem. Soc. 1983, 105, 3123-3126. (b) Bach, R. D.; Wolber, G. J. J. Am. Chem. Soc. 1984, 106, 1410-1415. (c) Davis, F. A.; Chattopadhyay, S. Tetrahedron Lett. 1986, 27, 5079-5082.
- (1984) J. Am. Chem. Soc. , vol.106 , pp. 1410-1415
- Bach, R.D.¹ Wolber, G.J.²

64
- 0001400976
- It is interesting to note that both experimental and theoretical studies suggested that the epoxidation of olefins with oxaziridine proceeded preferably via a planar transition state: (a) Davis, F. A.; Harakal, M. E.; Awad, S. B. J. Am. Chem. Soc. 1983, 105, 3123-3126. (b) Bach, R. D.; Wolber, G. J. J. Am. Chem. Soc. 1984, 106, 1410-1415. (c) Davis, F. A.; Chattopadhyay, S. Tetrahedron Lett. 1986, 27, 5079-5082.
- (1986) Tetrahedron Lett. , vol.27 , pp. 5079-5082
- Davis, F.A.¹ Chattopadhyay, S.²

65
- 0000776037
- (a) Chang, H.-T.; Sharpless, K. B. J. Org. Chem. 1996, 61, 6456-6457.
- (1996) J. Org. Chem. , vol.61 , pp. 6456-6457
- Chang, H.-T.¹ Sharpless, K.B.²

66
- 0001683725
- (b) Witkop, B.; Foltz, C. M. J. Am. Chem. Soc. 1957, 79, 197-201.
- (1957) J. Am. Chem. Soc. , vol.79 , pp. 197-201
- Witkop, B.¹ Foltz, C.M.²

67
- 1842343832
- See ref 10
- (c) See ref 10.

68
- 1842391291
- See ref 11
- (d) See ref 11.

69
- 0028136779
- (e) Tanner, D.; Birgersson, C.; Gogoll, A.; Luthman, K. Tetrahedron 1994, 50, 9797-9824.
- (1994) Tetrahedron , vol.50 , pp. 9797-9824
- Tanner, D.¹ Birgersson, C.² Gogoll, A.³ Luthman, K.⁴

70
- 0023141522
- (f) Compared with its dioxane analogues: Oehlschlager, A. C.; Johnston, B. D. J. Org. Chem. 1987, 52, 940-943.
- (1987) J. Org. Chem. , vol.52 , pp. 940-943
- Oehlschlager, A.C.¹ Johnston, B.D.²

71
- 1842320791
- (a) Reference 2d
- (a) Reference 2d.

72
- 0001193783
- (b) Berti, G, Macchia, B.; Macchia, F; Monti, L. J. Org. Chem. 1968, 33, 4045-4049.
- (1968) J. Org. Chem. , vol.33 , pp. 4045-4049
- Berti, G.¹ Macchia, B.² Macchia, F.³ Monti, L.⁴

73
- 33845182960
- (c) Satoh, T.; Oohara, T.; Ueda, Y.; Yamakawa, K. J. Org. Chem. 1989, 54, 3130-3136.
- (1989) J. Org. Chem. , vol.54 , pp. 3130-3136
- Satoh, T.¹ Oohara, T.² Ueda, Y.³ Yamakawa, K.⁴

74
- 0011896443
- (d) Tani, K.; Hanafusa, M.; Otsuka, S. Tetrahedron Letters 1979, 32, 3017-3020.
- (1979) Tetrahedron Letters , vol.32 , pp. 3017-3020
- Tani, K.¹ Hanafusa, M.² Otsuka, S.³

75
- 0343341049
- (e) Zhang, W.; Loebach, J. L.; Wilson, S. R.; Jacobsen, E. N. J. Am. Chem. Soc. 1990, 112, 2801-2803.
- (1990) J. Am. Chem. Soc. , vol.112 , pp. 2801-2803
- Zhang, W.¹ Loebach, J.L.² Wilson, S.R.³ Jacobsen, E.N.⁴

76
- 33845280252
- (a) Corey, E. J.; Shibata, S.; Bakshi, R. K. J. Org. Chem. 1988, 53, 2861-2863.
- (1988) J. Org. Chem. , vol.53 , pp. 2861-2863
- Corey, E.J.¹ Shibata, S.² Bakshi, R.K.³

77
- 0000178458
- (b) Chattopadhyay, S.; Mamdapur, V. R.; Chadha, M. S. Tetrahedron 1990, 46, 3667-3672.
- (1990) Tetrahedron , vol.46 , pp. 3667-3672
- Chattopadhyay, S.¹ Mamdapur, V.R.² Chadha, M.S.³

78
- 0025178915
- (c) Fujisawa, T.; Takemura, I.; Ukaji, Y. Tetrahedron Lett. 1990, 31, 5479-5482.
- (1990) Tetrahedron Lett. , vol.31 , pp. 5479-5482
- Fujisawa, T.¹ Takemura, I.² Ukaji, Y.³

79
- 37049110133
- (d) Akhtar, M. N.; Boyd, D. R.; Hamilton, J. G. J. Chem. Soc., Perkin Trans. 1, 1979, 2437-2440.
- (1979) J. Chem. Soc., Perkin Trans. 1 , pp. 2437-2440
- Akhtar, M.N.¹ Boyd, D.R.² Hamilton, J.G.³

80
- 4544372541
- PCT Int. Appl. W091 14,694, 1992; U.S. Appl. 496,992, 1992
- (e) Jacobsen, E. N.; Zhang, W. PCT Int. Appl. W091 14,694, 1992; U.S. Appl. 496,992, 1992; Chem. Abstr. 1992, 117, 106067f.
- (1992) Chem. Abstr. , vol.117
- Jacobsen, E.N.¹ Zhang, W.²

81
- 0009397316
- Tipson, R. S.; Brady, R. F., Jr.; West, B. F. Carbohydr. Res. 1971, 16, 383-393.
- (1971) Carbohydr. Res. , vol.16 , pp. 383-393
- Tipson, R.S.¹ Brady Jr., R.F.² West, B.F.³

82
- 37049132546
- James, K.; Tatchell, A. R.; Ray, P. K. J. Chem. Soc. (C) 1967, 2681-2686.
- (1967) J. Chem. Soc. (C) , pp. 2681-2686
- James, K.¹ Tatchell, A.R.² Ray, P.K.³

83
- 29644432244
- Corey, E. J.; Venkakeswarlu, A. J. Am. Chem. Soc. 1972, 94, 6190-6191.
- (1972) J. Am. Chem. Soc. , vol.94 , pp. 6190-6191
- Corey, E.J.¹ Venkakeswarlu, A.²

84
- 33747188908
- Chaudlrary, S. K.; Hernandez, O. Tetrahedron Lett. 1979, 95-98.
- (1979) Tetrahedron Lett. , pp. 95-98
- Chaudlrary, S.K.¹ Hernandez, O.²

85
- 0000671081
- Wiley: New York, Collect
- Daignault, R. A.; Eliel, E. L. Organic Syntheses; Wiley: New York, 1973; Collect Vol. V, pp 303-306.
- (1973) Organic Syntheses , vol.5 , pp. 303-306
- Daignault, R.A.¹ Eliel, E.L.²

86
- 1842274770
- Look, M. J. Chem. Ecol. 1976, 2, 83-86.
- (1976) J. Chem. Ecol. , vol.2 , pp. 83-86
- Look, M.¹

87
- 0017256953
- For racemate, see: Kocienski, P. J.; Ostrow, R. W. J. Org. Chem. 1976, 41, 398-399.
- (1976) J. Org. Chem. , vol.41 , pp. 398-399
- Kocienski, P.J.¹ Ostrow, R.W.²

88
- 0001685085
- Johnson, W. S.; Werthemann, L.; Bartlett, W. R.; Brocksom, T. J.; Li, T.-T. Faulkner, D. J.; Petersen, M. R. J. Am. Chem. Soc. 1970, 92, 741-743.
- (1970) J. Am. Chem. Soc. , vol.92 , pp. 741-743
- Johnson, W.S.¹ Werthemann, L.² Bartlett, W.R.³ Brocksom, T.J.⁴ Li, T.-T.⁵ Faulkner, D.J.⁶ Petersen, M.R.⁷

89
- 0342851774
- Barton, D. H. R.; Bohe, L.; Lusinchi, X. Tetrahedron 1990, 46, 5273-5284.
- (1990) Tetrahedron , vol.46 , pp. 5273-5284
- Barton, D.H.R.¹ Bohe, L.² Lusinchi, X.³

90
- 1842354658
- Calo, V.; Lopez, L.; Fiandanese, V.; Naso, F.; Ronzini, L. Tetrahedron Lett. 1978, 4963-4966.
- (1978) Tetrahedron Lett. , pp. 4963-4966
- Calo, V.¹ Lopez, L.² Fiandanese, V.³ Naso, F.⁴ Ronzini, L.⁵

91
- 0027513495
- For racemate, see: Bouhlel, E.; Laszlo, P.; Levart, M.; Montaufier, M.-T.; Singh, G. P. Tetrahedron Lett. 1993, 34, 1123-1126.
- (1993) Tetrahedron Lett. , vol.34 , pp. 1123-1126
- Bouhlel, E.¹ Laszlo, P.² Levart, M.³ Montaufier, M.-T.⁴ Singh, G.P.⁵

92
- 0000169587
- Tsunoda, T.; Suzuki, M.; Noyori, R. Tetrahedron Lett. 1980, 21, 1357-1358.
- (1980) Tetrahedron Lett. , vol.21 , pp. 1357-1358
- Tsunoda, T.¹ Suzuki, M.² Noyori, R.³

93
- 0028063655
- Doris, E.; Dechoux, L.; Mioskowski, C. Tetrahedron Lett. 1994, 35, 7943-7946.
- (1994) Tetrahedron Lett. , vol.35 , pp. 7943-7946
- Doris, E.¹ Dechoux, L.² Mioskowski, C.³

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.