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Journal of Organic Chemistry

Volumn 63, Issue 9, 1998, Pages 2948-2953

Highly Regio- and Enantioselective Monoepoxidation of Conjugated Dienes

(5) Frohn, Michael a Dalkiewicz, Molly a Tu, Yong a Wang, Zhi Xian a Shi, Yian a

a Immunology and Pathology (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000443501 PISSN: 00223263 EISSN: None Source Type: Journal
DOI: 10.1021/jo9721195 Document Type: Article

Times cited : (153)

References (44)

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8
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9
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- (1994) J. Am. Chem. Soc. , vol.116 , pp. 425-426
- Zhang, W.¹ Lee, N.H.² Jacobsen, E.N.³

10
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11
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12
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13
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16
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- For some examples of racemic epoxidations of conjugated dienes and polyenes with dimethyldioxirane see: (a) Curci, R.; Fiorentino, M.; Troisi, L.; Edwards, J. O.; Pater, R. H. J. Org. Chem. 1980, 45, 4758-4760. (b) Ebenezer, W.; Pattenden, G. Tetrahedron Lett. 1992, 33, 4053-4056. (c) Curci, R.; Detomaso, A.; Prencipe, T.; Carpenter, G. B. J. Am. Chem. Soc. 1994, 116, 8112-8115. (d) Curci, R.; Detomaso, A.; Lattanzio, M. E.; Carpenter, G. B. J. Am. Chem. Soc. 1996, 118, 11089-11092. (e) Murray, R. W.; Singh, M.; Rath, N. Tetrahedron Lett. 1996, 37, 8671-8674. (f) Murray, R. W.; Singh, M.; Rath, N. J. Org. Chem. 1997, 62, 8794-8799. (g) Yang, D.; Wong, M.-K.; Cheung, K.-K.; Chan, E. W. C.; Xie, Y. Tetrahedron Lett. 1997, 38, 6865-6868.
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17
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- For some examples of racemic epoxidations of conjugated dienes and polyenes with dimethyldioxirane see: (a) Curci, R.; Fiorentino, M.; Troisi, L.; Edwards, J. O.; Pater, R. H. J. Org. Chem. 1980, 45, 4758-4760. (b) Ebenezer, W.; Pattenden, G. Tetrahedron Lett. 1992, 33, 4053-4056. (c) Curci, R.; Detomaso, A.; Prencipe, T.; Carpenter, G. B. J. Am. Chem. Soc. 1994, 116, 8112-8115. (d) Curci, R.; Detomaso, A.; Lattanzio, M. E.; Carpenter, G. B. J. Am. Chem. Soc. 1996, 118, 11089-11092. (e) Murray, R. W.; Singh, M.; Rath, N. Tetrahedron Lett. 1996, 37, 8671-8674. (f) Murray, R. W.; Singh, M.; Rath, N. J. Org. Chem. 1997, 62, 8794-8799. (g) Yang, D.; Wong, M.-K.; Cheung, K.-K.; Chan, E. W. C.; Xie, Y. Tetrahedron Lett. 1997, 38, 6865-6868.
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18
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- For some examples of racemic epoxidations of conjugated dienes and polyenes with dimethyldioxirane see: (a) Curci, R.; Fiorentino, M.; Troisi, L.; Edwards, J. O.; Pater, R. H. J. Org. Chem. 1980, 45, 4758-4760. (b) Ebenezer, W.; Pattenden, G. Tetrahedron Lett. 1992, 33, 4053-4056. (c) Curci, R.; Detomaso, A.; Prencipe, T.; Carpenter, G. B. J. Am. Chem. Soc. 1994, 116, 8112-8115. (d) Curci, R.; Detomaso, A.; Lattanzio, M. E.; Carpenter, G. B. J. Am. Chem. Soc. 1996, 118, 11089-11092. (e) Murray, R. W.; Singh, M.; Rath, N. Tetrahedron Lett. 1996, 37, 8671-8674. (f) Murray, R. W.; Singh, M.; Rath, N. J. Org. Chem. 1997, 62, 8794-8799. (g) Yang, D.; Wong, M.-K.; Cheung, K.-K.; Chan, E. W. C.; Xie, Y. Tetrahedron Lett. 1997, 38, 6865-6868.
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19
- 0029862761
- For some examples of racemic epoxidations of conjugated dienes and polyenes with dimethyldioxirane see: (a) Curci, R.; Fiorentino, M.; Troisi, L.; Edwards, J. O.; Pater, R. H. J. Org. Chem. 1980, 45, 4758-4760. (b) Ebenezer, W.; Pattenden, G. Tetrahedron Lett. 1992, 33, 4053-4056. (c) Curci, R.; Detomaso, A.; Prencipe, T.; Carpenter, G. B. J. Am. Chem. Soc. 1994, 116, 8112-8115. (d) Curci, R.; Detomaso, A.; Lattanzio, M. E.; Carpenter, G. B. J. Am. Chem. Soc. 1996, 118, 11089-11092. (e) Murray, R. W.; Singh, M.; Rath, N. Tetrahedron Lett. 1996, 37, 8671-8674. (f) Murray, R. W.; Singh, M.; Rath, N. J. Org. Chem. 1997, 62, 8794-8799. (g) Yang, D.; Wong, M.-K.; Cheung, K.-K.; Chan, E. W. C.; Xie, Y. Tetrahedron Lett. 1997, 38, 6865-6868.
- (1996) J. Am. Chem. Soc. , vol.118 , pp. 11089-11092
- Curci, R.¹ Detomaso, A.² Lattanzio, M.E.³ Carpenter, G.B.⁴

20
- 0030602207
- For some examples of racemic epoxidations of conjugated dienes and polyenes with dimethyldioxirane see: (a) Curci, R.; Fiorentino, M.; Troisi, L.; Edwards, J. O.; Pater, R. H. J. Org. Chem. 1980, 45, 4758-4760. (b) Ebenezer, W.; Pattenden, G. Tetrahedron Lett. 1992, 33, 4053-4056. (c) Curci, R.; Detomaso, A.; Prencipe, T.; Carpenter, G. B. J. Am. Chem. Soc. 1994, 116, 8112-8115. (d) Curci, R.; Detomaso, A.; Lattanzio, M. E.; Carpenter, G. B. J. Am. Chem. Soc. 1996, 118, 11089-11092. (e) Murray, R. W.; Singh, M.; Rath, N. Tetrahedron Lett. 1996, 37, 8671-8674. (f) Murray, R. W.; Singh, M.; Rath, N. J. Org. Chem. 1997, 62, 8794-8799. (g) Yang, D.; Wong, M.-K.; Cheung, K.-K.; Chan, E. W. C.; Xie, Y. Tetrahedron Lett. 1997, 38, 6865-6868.
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- Murray, R.W.¹ Singh, M.² Rath, N.³

21
- 0344935543
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- (1997) J. Org. Chem. , vol.62 , pp. 8794-8799
- Murray, R.W.¹ Singh, M.² Rath, N.³

22
- 0030814478
- For some examples of racemic epoxidations of conjugated dienes and polyenes with dimethyldioxirane see: (a) Curci, R.; Fiorentino, M.; Troisi, L.; Edwards, J. O.; Pater, R. H. J. Org. Chem. 1980, 45, 4758-4760. (b) Ebenezer, W.; Pattenden, G. Tetrahedron Lett. 1992, 33, 4053-4056. (c) Curci, R.; Detomaso, A.; Prencipe, T.; Carpenter, G. B. J. Am. Chem. Soc. 1994, 116, 8112-8115. (d) Curci, R.; Detomaso, A.; Lattanzio, M. E.; Carpenter, G. B. J. Am. Chem. Soc. 1996, 118, 11089-11092. (e) Murray, R. W.; Singh, M.; Rath, N. Tetrahedron Lett. 1996, 37, 8671-8674. (f) Murray, R. W.; Singh, M.; Rath, N. J. Org. Chem. 1997, 62, 8794-8799. (g) Yang, D.; Wong, M.-K.; Cheung, K.-K.; Chan, E. W. C.; Xie, Y. Tetrahedron Lett. 1997, 38, 6865-6868.
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- Yang, D.¹ Wong, M.-K.² Cheung, K.-K.³ Chan, E.W.C.⁴ Xie, Y.⁵

23
- 0001407313
- For examples of the epoxidation of vinylsilanes with dimethyldioxirane see: (a) Branan, B. M.; Wang, X.; Jankowski, P.; Wicha, J.; Paquette, L. A. J. Org. Chem. 1994, 59, 6874-6876. (b) Adam, W.; Prechtl, F.; Richter, M. J.; Smerz, A. K. Tetrahedron Lett. 1995, 36, 4991-4994.
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24
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25
- 0000473362
- The silyl-substituted dienes were readily prepared on the basis of the reported method: Ni, Z. J.; Yang, P. F.; Ng, D. K. P.; Tzeng, Y. L.; Luh, T. Y. J. Am. Chem. Soc. 1990, 122, 9356-9364.
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26
- 85034467886
- In comparison, the diene of entry 17 was epoxidized with m-CPBA. The distal epoxide was favored by a 2.5:1 ratio
- In comparison, the diene of entry 17 was epoxidized with m-CPBA. The distal epoxide was favored by a 2.5:1 ratio.

27
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28
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29
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30
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31
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