First highly enantioselective epoxidation of alkenes with aldehyde/Oxone®

Tetrahedron Letters

Volumn 44, Issue 40, 2003, Pages 7403-7406

  Bez, Ghanashyam ^a   Zhao, Cong Gui ^a  

^a UNIVERSITY OF TEXAS AT SAN ANTONIO   (United States)

Author keywords

Aldehyde dioxirane; Alkene; Enantioselective; Epoxidation, Oxone

Indexed keywords

ALDEHYDE; ALKANE DERIVATIVE; ALKENE DERIVATIVE; DIOXIRANE; OXYGEN; UNCLASSIFIED DRUG;

ARTICLE; ASYMMETRIC CATALYSIS; CATALYSIS; CATALYST; ENANTIOSELECTIVITY; EPOXIDATION; GAS CHROMATOGRAPHY; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

EID: 0041834596     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2003.08.040     Document Type: Article

References (35)

1. For reviews, see: (a) Adam, W.; Saha-Möller, C. R.; Zhao, C.-G. Org. React. 2002, 61, 219-516; (b) Adam, W.; Smerz, A. K. Bull. Soc. Chim. Belg. 1996, 105, 581-599; (c) Curci, R.; Dinoi, A.; Rubino, M. F. Pure Appl. Chem. 1995, 67, 811-822; (d) Murray, R. W. Chem. Rev. 1989, 89, 1187-1201; (e) Adam, W.; Curci, R.; Edwards, J. O. Acc. Chem. Res. 1989, 22, 205-211.
2. For reviews, see: (a) Adam, W.; Saha-Möller, C. R.; Zhao, C.-G. Org. React. 2002, 61, 219-516; (b) Adam, W.; Smerz, A. K. Bull. Soc. Chim. Belg. 1996, 105, 581-599; (c) Curci, R.; Dinoi, A.; Rubino, M. F. Pure Appl. Chem. 1995, 67, 811-822; (d) Murray, R. W. Chem. Rev. 1989, 89, 1187-1201; (e) Adam, W.; Curci, R.; Edwards, J. O. Acc. Chem. Res. 1989, 22, 205-211.
3. For reviews, see: (a) Adam, W.; Saha-Möller, C. R.; Zhao, C.-G. Org. React. 2002, 61, 219-516; (b) Adam, W.; Smerz, A. K. Bull. Soc. Chim. Belg. 1996, 105, 581-599; (c) Curci, R.; Dinoi, A.; Rubino, M. F. Pure Appl. Chem. 1995, 67, 811-822; (d) Murray, R. W. Chem. Rev. 1989, 89, 1187-1201; (e) Adam, W.; Curci, R.; Edwards, J. O. Acc. Chem. Res. 1989, 22, 205-211.
4. For reviews, see: (a) Adam, W.; Saha-Möller, C. R.; Zhao, C.-G. Org. React. 2002, 61, 219-516; (b) Adam, W.; Smerz, A. K. Bull. Soc. Chim. Belg. 1996, 105, 581-599; (c) Curci, R.; Dinoi, A.; Rubino, M. F. Pure Appl. Chem. 1995, 67, 811-822; (d) Murray, R. W. Chem. Rev. 1989, 89, 1187-1201; (e) Adam, W.; Curci, R.; Edwards, J. O. Acc. Chem. Res. 1989, 22, 205-211.
5. For reviews, see: (a) Adam, W.; Saha-Möller, C. R.; Zhao, C.-G. Org. React. 2002, 61, 219-516; (b) Adam, W.; Smerz, A. K. Bull. Soc. Chim. Belg. 1996, 105, 581-599; (c) Curci, R.; Dinoi, A.; Rubino, M. F. Pure Appl. Chem. 1995, 67, 811-822; (d) Murray, R. W. Chem. Rev. 1989, 89, 1187-1201; (e) Adam, W.; Curci, R.; Edwards, J. O. Acc. Chem. Res. 1989, 22, 205-211.
6. For reviews, see: (a) Frohn, M.; Shi, Y. Synthesis 2000, 1979-2000; (b) Adam, W.; Degen, H. G.; Pastor, A.; Saha-Möller, C. R.; Schambony, S. B.; Zhao, C.-G. In Peroxide Chemistry; Adam, W., Ed.; Wiley-VCH: Weinheim, 2000, pp. 78-112; (c) Denmark, S. E.; Wu, Z. Synlett 1999, 847-859; (d) Ref. 1a.
7. For reviews, see: (a) Frohn, M.; Shi, Y. Synthesis 2000, 1979-2000; (b) Adam, W.; Degen, H. G.; Pastor, A.; Saha-Möller, C. R.; Schambony, S. B.; Zhao, C.-G. In Peroxide Chemistry; Adam, W., Ed.; Wiley-VCH: Weinheim, 2000, pp. 78-112; (c) Denmark, S. E.; Wu, Z. Synlett 1999, 847-859; (d) Ref. 1a.
8. For reviews, see: (a) Frohn, M.; Shi, Y. Synthesis 2000, 1979-2000; (b) Adam, W.; Degen, H. G.; Pastor, A.; Saha-Möller, C. R.; Schambony, S. B.; Zhao, C.-G. In Peroxide Chemistry; Adam, W., Ed.; Wiley-VCH: Weinheim, 2000, pp. 78-112; (c) Denmark, S. E.; Wu, Z. Synlett 1999, 847-859; (d) Ref. 1a.
9. For reviews, see: (a) Frohn, M.; Shi, Y. Synthesis 2000, 1979-2000; (b) Adam, W.; Degen, H. G.; Pastor, A.; Saha-Möller, C. R.; Schambony, S. B.; Zhao, C.-G. In Peroxide Chemistry; Adam, W., Ed.; Wiley-VCH: Weinheim, 2000, pp. 78-112; (c) Denmark, S. E.; Wu, Z. Synlett 1999, 847-859; (d) Ref. 1a.
10. For most recent examples, see: (a) Shu, L.; Wang, P.; Gan, Y.; Shi, Y. Org. Lett. 2003, 5, 293-296; (b) Tian, H.; She, X.; Yu, H.; Shu, L.; Shi, Y. J. Org. Chem. 2002, 67, 2435-2446; (c) Shing, T. K. M.; Leung, G. Y. C. Tetrahedron 2002, 58, 7545-7552; (d) Denmark, S. E.; Matsuhashi, H. J. Org. Chem. 2002, 67, 3479-3486; (e) Stearman, C. J.; Behar, V. Tetrahedron Lett. 2002, 43, 1943-1946; (f) Matsumoto, K.; Tomioka, K. Tetrahedron Lett. 2002, 43, 631-633; (g) Tian, H.; She, X.; Xu, J.; Shi, Y. Org. Lett. 2001, 3, 1929-1931; (h) Armstrong, A.; Moss, W. O.; Reeves, J. R. Tetrahedron: Asymmetry 2001, 12, 2779-2781; (i) Seki, M.; Furutani, T.; Imashiro, R.; Kuroda, T.; Yamanaka, T.; Harada, N.; Arakawa, H.; Kusama, M.; Hashiyama, T. Tetrahedron Lett. 2001, 42, 8201-8205.
11. For most recent examples, see: (a) Shu, L.; Wang, P.; Gan, Y.; Shi, Y. Org. Lett. 2003, 5, 293-296; (b) Tian, H.; She, X.; Yu, H.; Shu, L.; Shi, Y. J. Org. Chem. 2002, 67, 2435-2446; (c) Shing, T. K. M.; Leung, G. Y. C. Tetrahedron 2002, 58, 7545-7552; (d) Denmark, S. E.; Matsuhashi, H. J. Org. Chem. 2002, 67, 3479-3486; (e) Stearman, C. J.; Behar, V. Tetrahedron Lett. 2002, 43, 1943-1946; (f) Matsumoto, K.; Tomioka, K. Tetrahedron Lett. 2002, 43, 631-633; (g) Tian, H.; She, X.; Xu, J.; Shi, Y. Org. Lett. 2001, 3, 1929-1931; (h) Armstrong, A.; Moss, W. O.; Reeves, J. R. Tetrahedron: Asymmetry 2001, 12, 2779-2781; (i) Seki, M.; Furutani, T.; Imashiro, R.; Kuroda, T.; Yamanaka, T.; Harada, N.; Arakawa, H.; Kusama, M.; Hashiyama, T. Tetrahedron Lett. 2001, 42, 8201-8205.
12. For most recent examples, see: (a) Shu, L.; Wang, P.; Gan, Y.; Shi, Y. Org. Lett. 2003, 5, 293-296; (b) Tian, H.; She, X.; Yu, H.; Shu, L.; Shi, Y. J. Org. Chem. 2002, 67, 2435-2446; (c) Shing, T. K. M.; Leung, G. Y. C. Tetrahedron 2002, 58, 7545-7552; (d) Denmark, S. E.; Matsuhashi, H. J. Org. Chem. 2002, 67, 3479-3486; (e) Stearman, C. J.; Behar, V. Tetrahedron Lett. 2002, 43, 1943-1946; (f) Matsumoto, K.; Tomioka, K. Tetrahedron Lett. 2002, 43, 631-633; (g) Tian, H.; She, X.; Xu, J.; Shi, Y. Org. Lett. 2001, 3, 1929-1931; (h) Armstrong, A.; Moss, W. O.; Reeves, J. R. Tetrahedron: Asymmetry 2001, 12, 2779-2781; (i) Seki, M.; Furutani, T.; Imashiro, R.; Kuroda, T.; Yamanaka, T.; Harada, N.; Arakawa, H.; Kusama, M.; Hashiyama, T. Tetrahedron Lett. 2001, 42, 8201-8205.
13. For most recent examples, see: (a) Shu, L.; Wang, P.; Gan, Y.; Shi, Y. Org. Lett. 2003, 5, 293-296; (b) Tian, H.; She, X.; Yu, H.; Shu, L.; Shi, Y. J. Org. Chem. 2002, 67, 2435-2446; (c) Shing, T. K. M.; Leung, G. Y. C. Tetrahedron 2002, 58, 7545-7552; (d) Denmark, S. E.; Matsuhashi, H. J. Org. Chem. 2002, 67, 3479-3486; (e) Stearman, C. J.; Behar, V. Tetrahedron Lett. 2002, 43, 1943-1946; (f) Matsumoto, K.; Tomioka, K. Tetrahedron Lett. 2002, 43, 631-633; (g) Tian, H.; She, X.; Xu, J.; Shi, Y. Org. Lett. 2001, 3, 1929-1931; (h) Armstrong, A.; Moss, W. O.; Reeves, J. R. Tetrahedron: Asymmetry 2001, 12, 2779-2781; (i) Seki, M.; Furutani, T.; Imashiro, R.; Kuroda, T.; Yamanaka, T.; Harada, N.; Arakawa, H.; Kusama, M.; Hashiyama, T. Tetrahedron Lett. 2001, 42, 8201-8205.
14. For most recent examples, see: (a) Shu, L.; Wang, P.; Gan, Y.; Shi, Y. Org. Lett. 2003, 5, 293-296; (b) Tian, H.; She, X.; Yu, H.; Shu, L.; Shi, Y. J. Org. Chem. 2002, 67, 2435-2446; (c) Shing, T. K. M.; Leung, G. Y. C. Tetrahedron 2002, 58, 7545-7552; (d) Denmark, S. E.; Matsuhashi, H. J. Org. Chem. 2002, 67, 3479-3486; (e) Stearman, C. J.; Behar, V. Tetrahedron Lett. 2002, 43, 1943-1946; (f) Matsumoto, K.; Tomioka, K. Tetrahedron Lett. 2002, 43, 631-633; (g) Tian, H.; She, X.; Xu, J.; Shi, Y. Org. Lett. 2001, 3, 1929-1931; (h) Armstrong, A.; Moss, W. O.; Reeves, J. R. Tetrahedron: Asymmetry 2001, 12, 2779-2781; (i) Seki, M.; Furutani, T.; Imashiro, R.; Kuroda, T.; Yamanaka, T.; Harada, N.; Arakawa, H.; Kusama, M.; Hashiyama, T. Tetrahedron Lett. 2001, 42, 8201-8205.
15. For most recent examples, see: (a) Shu, L.; Wang, P.; Gan, Y.; Shi, Y. Org. Lett. 2003, 5, 293-296; (b) Tian, H.; She, X.; Yu, H.; Shu, L.; Shi, Y. J. Org. Chem. 2002, 67, 2435-2446; (c) Shing, T. K. M.; Leung, G. Y. C. Tetrahedron 2002, 58, 7545-7552; (d) Denmark, S. E.; Matsuhashi, H. J. Org. Chem. 2002, 67, 3479-3486; (e) Stearman, C. J.; Behar, V. Tetrahedron Lett. 2002, 43, 1943-1946; (f) Matsumoto, K.; Tomioka, K. Tetrahedron Lett. 2002, 43, 631-633; (g) Tian, H.; She, X.; Xu, J.; Shi, Y. Org. Lett. 2001, 3, 1929-1931; (h) Armstrong, A.; Moss, W. O.; Reeves, J. R. Tetrahedron: Asymmetry 2001, 12, 2779-2781; (i) Seki, M.; Furutani, T.; Imashiro, R.; Kuroda, T.; Yamanaka, T.; Harada, N.; Arakawa, H.; Kusama, M.; Hashiyama, T. Tetrahedron Lett. 2001, 42, 8201-8205.
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