An efficient catalyst for asymmetric epoxidation of terminal olefins

Journal of the American Chemical Society

Volumn 121, Issue 2, 1999, Pages 460-461

  Collman, James P ^a   Wang, Zhong ^a   Straumanis, Andrei ^a   Quelquejeu, Mélanie ^a   Rose, Eric ^b  

^a STANFORD UNIVERSITY   (United States)

^b CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE DERIVATIVE;

ARTICLE; CATALYST; CHIRALITY; ENANTIOMER; EPOXIDATION; ISOMER; LIGAND BINDING; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0033585578     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9818699     Document Type: Article

References (21)

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14. There was only one previous example of chiral Fe porphyrin with an ααβα geometry, which gave no chiral induction due to the flexible conformations of the chiral pickets. Groves, J. T.; Myers, R. S. J. Am. Chem. Soc. 1983, 105, 5791.
15. Rose, E.; Cardon-Pilotaz, A.; Quelquejeu, M.; Bernard, N.; Kossanyi, A.; Desmazières, B. J. Org. Chem. 1995, 60, 3919.
16. The identity of 1 was established by MS, UV - visible spectra, and conversion to its metal-free form.
17. A comparison has been made between 1 and a closely related Fe porphyrin complex, amide-linked "twin-coronet" porphyrin derived from tetrakis(2,6-diamino-4-tert-butylphenyl)porphyrin. 1 gives both a higher % ee and a greater reaction rate. See also: Naruta, Y.; Tani, F.; Maruyama, K. Tetrahedron Lett. 1992, 33, 6323.
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19. Collman, J. P.; Chien, A.; Eberspacher, T. Unpublished results.
20. Epoxidation of styrene with a recovered catalyst or a catalyst premodified by stirring with cyclopentene and PhIO does give higher ee (83%) even at low turnover numbers.
21. A slightly higher ee % value was obtained in the initial stages of epoxidation of styrene catalyzed by a chiral Fe porphyrin. Groves, J. T.; Crowley, S. J.; Shalyaev, K. V. Chirality 1998, 10, 106.