Chromium salen catalysed asymmetric alkene epoxidation. Influence of substituents at the 3,3'-positions on the salen rings

Tetrahedron Letters

Volumn 40, Issue 18, 1999, Pages 3613-3616

  Ryan, Kenneth M ^a   Bousquet, Claudine ^a   Gilheany, Declan G ^a  

^a UNIVERSITY COLLEGE DUBLIN   (Ireland)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; BETA METHYLSTYRENE; CHROMIUM; CHROMIUM DERIVATIVE; LIGAND; SALEN; STYRENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL MODIFICATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; EPOXIDATION; ISOMERISM; REACTION ANALYSIS; STOICHIOMETRY; STRUCTURE ACTIVITY RELATION; STRUCTURE ANALYSIS;

EID: 0033617258     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00488-8     Document Type: Article

References (19)

1. 1. Bousquet, C.; Gilheany, D.G. Tetrahedron Lett. 1995, 36, 7739-7742
2. 2. Reported as a series of oral presentations at 211th National Meeting of the American Chemical Society, New Orleans, March 24-28th, 1996; ORGN 161-165, Dalton, C.T.; Ryan, K.M.; Coyne, E.J.; Wall, V.M.; Bousquet, C.; Gilheany, D.G.
3. 3. Jacobsen, E.N. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: Weinheim, 1993; Ch. 4.2, pp 159-202.
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6. 6. A similar proposal was made by: Norrby, P.O.; Linde, C.; Åkermark, B. J. Am Chem. Soc. 1995, 117, 11035-11036.
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9. 9. Houk, K.N.; DeMello, N.C.; Condroski, K.; Fennen, J.; Kasuga, T. in: Electronic Conference on Heterocyclic Chemistry, ECHET96, eds. Rzepa, H.S.; Snyder, J.P.; Leach, C. RSC, London, 24/6-22/7, 1996: http://www.ch.ic.ac.uk/ectoc/echet96/
10. 10. We have reviewed the history of metal salen complexes as asymmetric epoxidation catalysts and present state of understanding of their mechanism: Dalton, C.T.; Ryan, K.M.; Wall, V. M.; Bousquet, C.; Gilheany, D.G. Topics in Catalysis, 1998, 5, 75-91.
11. 11. Zhang, W.; Loebach, J.L; Wilson, S.R.; Jacobsen, E.N. J. Am. Chem. Soc. 1990, 112, 2801-2803
12. 12. E-and Z-1,2-disubstituted alkenes are referred to as trans-and cis-alkenes respectively.
13. 13. (a) Irie, R.; Noda, K.; Ito, Y.; Matsumoto, N.; Katsuki, T. Tetrahedron Lett. 1990, 31, 7345-7348;
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16. 2O), analysis was by glc on a Supelco α-cyclodextrin capillary column with n-decane as internal standard. Catalytic oxidation: a mixture of alkene (0.43 mmol), donor ligand L (0.043 mmol) and Cr(III)salen hexafluorophosphate complex (0.043 mmol) in acetonitrile (3 ml) was treated at room temperature with iodosylbenzene (0.43 mmol) and worked up as above.
17. 15. Samsel, E.G.; Srinivasan, K.; Kochi, J.K. J. Am. Chem. Soc. 1985, 107, 7606-7617.
18. 16. Martinez, L.E.; Leighton, J.L.; Carsten, D.H.; Jacobsen, E.N. J. Am. Chem. Soc. 1995, 117, 5897-98.
19. 17. It is an understatement to say that these complexes do not crystallise well. So in common with all previous workers in this area (very few of whom have recorded analytical data) we have found it extremely difficult to prepare analytically pure material. We estimate that our initially prepared complexes are contaminated with 2-5% of presently unidentified material.