Unsymmetrical salen ligands: Synthesis and use in chromium mediated asymmetric epoxidation

Tetrahedron Letters

Volumn 40, Issue 18, 1999, Pages 3617-3620

  Daly, Adrian M ^a   Dalton, Cormac T ^a   Renehan, Marie F ^a   Gilheany, Declan G ^a  

^a UNIVERSITY COLLEGE DUBLIN   (Ireland)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE DERIVATIVE; CHROMIUM; LIGAND; PHOSPHINE OXIDE DERIVATIVE; SALEN; SALICYLIC ACID DERIVATIVE; TARTARIC ACID DERIVATIVE; TRIPHENYLPHOSPHINE OXIDE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; EPOXIDATION; REACTION ANALYSIS; STOICHIOMETRY; STRUCTURE ACTIVITY RELATION; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0033617329     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00489-X     Document Type: Article

References (19)

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2. 1. Canali, L.; Sherrington, D.C. Chem. Soc. Rev. 1999, in press; Dalton, C.T.; Ryan, K.M.; Wall, V.M.; Bousquet, C.; Gilheany, D.G.Topics in Catalysis 1998, 5, 75-91; Muñiz-Fernandez, K.; Bolm, C. Chapter 2.7.2 in Transition Metals for OrganicSynthesis Beller, M.; Bolm, C., Eds.; VCH, Weinheim, 1998; vol. 2, pp 271-282; Tokunaga, M.; Larrow, J.F.; Kakiuchi, F.;Jacobsen, E.N. Science 1997, 277, 936-938; Katsuki, T. Coord. Chem. Rev. 1995, 140, 189-214; Jacobsen, E.N. Chapter 4.2 inCatalytic Asymmetric Synthesis; Ojima, I. Ed.; VCH: Weinheim, 1993; pp. 159-202; Sigman, M.S.; Jacobsen, E.N. J. Am. Chem.Soc. 1998, 120, 5315-5316
3. 1. Canali, L.; Sherrington, D.C. Chem. Soc. Rev. 1999, in press; Dalton, C.T.; Ryan, K.M.; Wall, V.M.; Bousquet, C.; Gilheany, D.G.Topics in Catalysis 1998, 5, 75-91; Muñiz-Fernandez, K.; Bolm, C. Chapter 2.7.2 in Transition Metals for Organic Synthesis Beller, M.; Bolm, C., Eds.; VCH, Weinheim, 1998; vol. 2, pp 271-282; Tokunaga, M.; Larrow, J.F.; Kakiuchi, F.;Jacobsen, E.N. Science 1997, 277, 936-938; Katsuki, T. Coord. Chem. Rev. 1995, 140, 189-214; Jacobsen, E.N. Chapter 4.2 inCatalytic Asymmetric Synthesis; Ojima, I. Ed.; VCH: Weinheim, 1993; pp. 159-202; Sigman, M.S.; Jacobsen, E.N. J. Am. Chem.Soc. 1998, 120, 5315-5316
4. 1. Canali, L.; Sherrington, D.C. Chem. Soc. Rev. 1999, in press; Dalton, C.T.; Ryan, K.M.; Wall, V.M.; Bousquet, C.; Gilheany, D.G.Topics in Catalysis 1998, 5, 75-91; Muñiz-Fernandez, K.; Bolm, C. Chapter 2.7.2 in Transition Metals for OrganicSynthesis Beller, M.; Bolm, C., Eds.; VCH, Weinheim, 1998; vol. 2, pp 271-282; Tokunaga, M.; Larrow, J.F.; Kakiuchi, F.; Jacobsen, E.N. Science 1997, 277, 936-938; Katsuki, T. Coord. Chem. Rev. 1995, 140, 189-214; Jacobsen, E.N. Chapter 4.2 inCatalytic Asymmetric Synthesis; Ojima, I. Ed.; VCH: Weinheim, 1993; pp. 159-202; Sigman, M.S.; Jacobsen, E.N. J. Am. Chem.Soc. 1998, 120, 5315-5316
5. 1. Canali, L.; Sherrington, D.C. Chem. Soc. Rev. 1999, in press; Dalton, C.T.; Ryan, K.M.; Wall, V.M.; Bousquet, C.; Gilheany, D.G.Topics in Catalysis 1998, 5, 75-91; Muñiz-Fernandez, K.; Bolm, C. Chapter 2.7.2 in Transition Metals for OrganicSynthesis Beller, M.; Bolm, C., Eds.; VCH, Weinheim, 1998; vol. 2, pp 271-282; Tokunaga, M.; Larrow, J.F.; Kakiuchi, F.;Jacobsen, E.N. Science 1997, 277, 936-938; Katsuki, T. Coord. Chem. Rev. 1995, 140, 189-214; Jacobsen, E.N. Chapter 4.2 inCatalytic Asymmetric Synthesis; Ojima, I. Ed.; VCH: Weinheim, 1993; pp. 159-202; Sigman, M.S.; Jacobsen, E.N. J. Am. Chem.Soc. 1998, 120, 5315-5316
6. 1. Canali, L.; Sherrington, D.C. Chem. Soc. Rev. 1999, in press; Dalton, C.T.; Ryan, K.M.; Wall, V.M.; Bousquet, C.; Gilheany, D.G.Topics in Catalysis 1998, 5, 75-91; Muñiz-Fernandez, K.; Bolm, C. Chapter 2.7.2 in Transition Metals for OrganicSynthesis Beller, M.; Bolm, C., Eds.; VCH, Weinheim, 1998; vol. 2, pp 271-282; Tokunaga, M.; Larrow, J.F.; Kakiuchi, F.;Jacobsen, E.N. Science 1997, 277, 936-938; Katsuki, T. Coord. Chem. Rev. 1995, 140, 189-214; Jacobsen, E.N. Chapter 4.2 in Catalytic Asymmetric Synthesis; Ojima, I. Ed.; VCH: Weinheim, 1993; pp. 159-202; Sigman, M.S.; Jacobsen, E.N. J. Am. Chem.Soc. 1998, 120, 5315-5316
7. 1. Canali, L.; Sherrington, D.C. Chem. Soc. Rev. 1999, in press; Dalton, C.T.; Ryan, K.M.; Wall, V.M.; Bousquet, C.; Gilheany, D.G.Topics in Catalysis 1998, 5, 75-91; Muñiz-Fernandez, K.; Bolm, C. Chapter 2.7.2 in Transition Metals for OrganicSynthesis Beller, M.; Bolm, C., Eds.; VCH, Weinheim, 1998; vol. 2, pp 271-282; Tokunaga, M.; Larrow, J.F.; Kakiuchi, F.;Jacobsen, E.N. Science 1997, 277, 936-938; Katsuki, T. Coord. Chem. Rev. 1995, 140, 189-214; Jacobsen, E.N. Chapter 4.2 inCatalytic Asymmetric Synthesis; Ojima, I. Ed.; VCH: Weinheim, 1993; pp. 159-202; Sigman, M.S.; Jacobsen, E.N. J. Am. Chem. Soc. 1998, 120, 5315-5316
8. 2 Lopez, J.; Liang, S.; Bu, X.R. Tetrahedron Lett. 1998, 39, 4199-4202.
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10. 1H-nmr signals quoted for 2 (R=H) is not consistent with the assigned structure (there being too many), but quite consistent with a mixture of mono-and bis-products. Indeed in our hands and strictly following their procedure, just such a mixture was formed in a 3:1 ratio. Attempted condensation of this mixture with 3,5-di-tert-butylsalicylaldehyde, also used by Lopez et al., yields a 4:3:3 mixture of the unsymmetrical ligand and the two symmetrical ligands. The fact that a correct elemental analysis is quoted does not necessarily indicate the presence of pure unsymmetrical ligand since a mixture of the three possible Schiff bases will also give the same analysis.
11. 5 Bousquet, C.; Gilheany, D.G. Tetrahedron Lett. 1995, 42, 7739-42;
12. 6. 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.
13. 7. Ryan, K.M.; Bousquet, C.; Gilheany, D.G. Tetrahedron Lett. preceding paper.
14. 8. E-and Z-1,2-disubstituted alkenes are referred to as trans-and cis-alkenes respectively.
15. 9. Collman, J.P.; Zhang, X.; Lee, V.J.; Uffelman, E.S.; Brauman, J.I. Science 1993, 263, 1404-1411; Groves, J.T.; Nemo, T.E. J.Am Chem. Soc. 1983, 105, 5786-5791.
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17. 3, TMS): 1.19-1.96 (m, 26H), 3.22-3.31 (m, 1H), 3.36-3.46 (m, 1H), 6.66-6.69 (m, 1H), 6.98-7.05 (m, 2H), 7.31-7.35 (m, 2H), 8.25 (s,1H), 8.26 (s,1H), 13.54 (s, 1H), 14.35 (s, 1H). 2 (R=3,5 Cl) and consequently 4 were synthesised similarly.
18. -) complexes were synthesised according to Martinez, L.E.; Leighton, J.L.; Carsten, D.H.; Jacobsen, E.N. J. Am. Chem. Soc. 1995, 117, 5897-98. From this 5a was synthesised: to a solution of the chromium salen chloride complex (1 equivalent) in sufficient methanol, a solution of potassium hexafluoropnosphate (1.5 equivalent) in water (10 mL) was added dropwise. The resulting solution was stirred overnight and concentrated in vacuo to 10-15 mL. The final precipitate was collected by filtration, washed with water (2 × 10 mL) and dried in an oven at 100 °C. 5b was synthesised similarly using silver nitrate.
19. 12. Samsel, E.G.; Srinivasan, K.; Kochi, J.K. J. Am. Chem. Soc. 1985, 107, 7506-7617.