Enantioselective Olefin Epoxidation with Chiral Manganese/1,4,7-Triazacyclononane Complexes 1

Synlett

Volumn 1997, Issue 6, 1997, Pages 687-688

  Bolm, Carsten ^a   Kadereit, Dieter ^a   Valacchi, Michela ^a  

^a RWTH AACHEN UNIVERSITY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002095597     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-3244     Document Type: Article

References (27)

1. This paper is dedicated to Prof. Dr. F. Asinger on the occasion of his 90th birthday.
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10. For recent leading references: a) Belal, A. A.; Chaudhuri, P.; Fallis, I.; Farrugia, L. J.; Hartung, R.; Macdonald, N. M.; Nuber, B.; Peacock, R. D.; Weiss, J.; Wieghardt, K. Inorg. Chem. 1991, 30, 4397. b) Adam, B.; Bill, E.; Bothe, E.; Goerdt, B.; Haselhorst, G.; Hildenbrand, K.; Sokolowski, A.; Steenken, S.; Weyhermüller, T.; Wieghardt, K. Chem. Eur. J. 1997, 3, 308. c) Belal, A. A.; Farrugia, L. J.; Peacock, R. D.; Robb, J. J. Chem. Soc. Dalton Trans 1989, 931. d) Smith, G. T.; Mallinsson, P. R.; Peacock, R. D.; Farrugia, L. J.; Fallis, I. A.; Frampton, C. S.; Howard, J. A. K. J. Chem. Soc. Chem. Commun. 1996, 525.
11. For recent leading references: a) Belal, A. A.; Chaudhuri, P.; Fallis, I.; Farrugia, L. J.; Hartung, R.; Macdonald, N. M.; Nuber, B.; Peacock, R. D.; Weiss, J.; Wieghardt, K. Inorg. Chem. 1991, 30, 4397. b) Adam, B.; Bill, E.; Bothe, E.; Goerdt, B.; Haselhorst, G.; Hildenbrand, K.; Sokolowski, A.; Steenken, S.; Weyhermüller, T.; Wieghardt, K. Chem. Eur. J. 1997, 3, 308. c) Belal, A. A.; Farrugia, L. J.; Peacock, R. D.; Robb, J. J. Chem. Soc. Dalton Trans 1989, 931. d) Smith, G. T.; Mallinsson, P. R.; Peacock, R. D.; Farrugia, L. J.; Fallis, I. A.; Frampton, C. S.; Howard, J. A. K. J. Chem. Soc. Chem. Commun. 1996, 525.
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19. Recently it was shown that a dinuclear manganese(IV) catalyst with ligand 1 (R = Me) is capable to oxidize benzylic alcohols to aldehydes: Zondervan, C.; Hage, R.; Feringa, B. L. J. Chem. Soc. Chem. Commun. 1997, 419.
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22. 4). The conversions and ee-values were determined by GLC using Cyclodex-β-HP for styrene oxide (4), Lipodex-E for β-methylstyrene oxides (6) and Lipodex-B for chromene oxide 8.
23. For leading references: a) Zhang, W.; Lee, N. H.; Jacobsen, E. N. J. Am. Chem. Soc. 1994, 116, 425. b) Fu, H.; Look, G. C.; Zhang, W.; Jacobsen, E. N.; Wong, C. -H. J. Org. Chem. 1991, 56, 6497. c) Jacobsen, E. N.; Deng, L.; Furukawa, Y.; Martínez, L. E. Tetrahedron 1994, 50, 4323. d) Hamada, T.; Fukuda, T.; Imanishi, H.; Katsuki, T. Tetrahedron 1996, 52, 515 and references therein.
24. For leading references: a) Zhang, W.; Lee, N. H.; Jacobsen, E. N. J. Am. Chem. Soc. 1994, 116, 425. b) Fu, H.; Look, G. C.; Zhang, W.; Jacobsen, E. N.; Wong, C. -H. J. Org. Chem. 1991, 56, 6497. c) Jacobsen, E. N.; Deng, L.; Furukawa, Y.; Martínez, L. E. Tetrahedron 1994, 50, 4323. d) Hamada, T.; Fukuda, T.; Imanishi, H.; Katsuki, T. Tetrahedron 1996, 52, 515 and references therein.
25. For leading references: a) Zhang, W.; Lee, N. H.; Jacobsen, E. N. J. Am. Chem. Soc. 1994, 116, 425. b) Fu, H.; Look, G. C.; Zhang, W.; Jacobsen, E. N.; Wong, C. -H. J. Org. Chem. 1991, 56, 6497. c) Jacobsen, E. N.; Deng, L.; Furukawa, Y.; Martínez, L. E. Tetrahedron 1994, 50, 4323. d) Hamada, T.; Fukuda, T.; Imanishi, H.; Katsuki, T. Tetrahedron 1996, 52, 515 and references therein.
26. For leading references: a) Zhang, W.; Lee, N. H.; Jacobsen, E. N. J. Am. Chem. Soc. 1994, 116, 425. b) Fu, H.; Look, G. C.; Zhang, W.; Jacobsen, E. N.; Wong, C. -H. J. Org. Chem. 1991, 56, 6497. c) Jacobsen, E. N.; Deng, L.; Furukawa, Y.; Martínez, L. E. Tetrahedron 1994, 50, 4323. d) Hamada, T.; Fukuda, T.; Imanishi, H.; Katsuki, T. Tetrahedron 1996, 52, 515 and references therein.
27. The absolute configuration of the cis-epoxide remained undetermined.