Bis(oxazoline) as Chiral Ligand

No.107(January 2003)

I0567: (S,S)-(-)-2,2'-Isopropylidenebis(4-tert-butyl-2-oxazoline) (1)

C₂-Symmetric bisoxazoline 1 is a useful chiral ligand for enantiocontrol of metal-catalyzed reactions. For example, the chiral Cu(I) complex, which is generated from 1 and copper(I) triflate, is applied to asymmetric cyclopropanation of olefins and affords trans-diastereomers with high enantioselectivity.¹⁾ The reaction was used for total syntheses of (+)- and (-)-Scopadulcic acid A.²⁾

Recently, Cu(II) complex of 1 have been successfully employed as enantioselective Lewis acid catalyst in Diels-Alder reactions,³⁾ Aldol additions,⁴⁾ and Michael additions.⁵⁾

References

1)Bis(oxazolines) as chiral ligand
- D. A. Evans, K. A. Woerpel, M. M. Hinman, M. M. Faul, J. Am. Chem. Soc. 1991, 113, 726.
2)Total syntheses of (+)- and (-)-Scopadulcic Acid A
- M. E. Fox, C. Li, J. P. Marino, Jr., L. E. Overman, J. Am. Chem. Soc. 1999, 121, 5467.
3)Enantioselective Diels-Alder Reactions
- D. A. Evans, S. J. Miller, T. Lectka, P. von Matt., J. Am. Chem. Soc. 1999, 121, 7559.
- D. A. Evans, D. M. Barnes, J. S. Johnson, T. Lectka, P. von Matt, S. J. Miller, J. A. Murry, R. D. Norcross, E. A. Shaughnessy, K. R. Campos, ibid. 1999, 121, 7582.
4)Enantioselective aldol additions of enolsilanes
- D. A. Evans, M. C. Kozlowski, J. A. Murry, C. S. Burgey, K. R. Campos, B. T. Connell, R. J. Staples, J. Am. Chem. Soc. 1999, 121, 669.
- D. A. Evans, C. S. Burgey, M. C. Kozlowski, S.W. Tregay, ibid. 1999, 121, 686.
5)Enantioselective Michael Additions of enolsilanes to unsaturated ester derivatives
- D. A. Evans, M. C. Willis, J. N. Johnston, Org. Lett. 1999, 1, 865.

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Bis(oxazoline) as Chiral Ligand

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