Asymmetric Oxygenation of Chiral Imide Enolates. A General Approach to the Synthesis of Enantiomerically Pure a-Hydroxy Carboxylic Acid Synthons

Journal of the American Chemical Society

Volumn 107, Issue 14, 1985, Pages 4346-4348

  Evans, D A ^a   Morrissey, M M ^a   Dorow, R L ^a  

^a HARVARD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001594845     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00300a054     Document Type: Article

References (14)

1. Hanessian, S. “Total Synthesis of Natural Products: The Chiron Approach”; Pergamon Press: New York, 1983; Chapter 2.
2. Sharpless, K. B.; Katsuki, T. J. Am. Chem. Soc. 1980, 102, 5974.
3. Masamune, S.; Chow, W. Adrichimica Acta 1982, 15, 47.
4. Helmchen, G.; Wierzchowski, R. Angew. Chem., Int. Ed. Engl. 1984, 23, 60.
5. Kelly, T. R.; Arvanitis, A. Tetrahedron Lett. 1984, 25, 39.
6. Gamboni, R.; Mohr, P.; Waespe-Sarcevic, N.; Tamm, C. Tetrahedron Lett. 1985, 26, 203.
7. For a recent review, see: Evans, D. A. Aldrichimica Acta 1982, 15, 23. (b) Evans, D. A.; Ennis, M. D.; Mathre, D. J. J. Am. Chem. Soc. 1982, 104, 1737.
8. Davis, F. A.; Vishwakarma, L. C.; Billmers, J. M.; Finn, J. J. Org. Chem. 1984, 49, 3241.
9. Davis, F. A.; Lamendola, J., Jr.; Nadir, U.; Kluger, E. W.; Sedergran, T. C.; Panunto, T. W.; Billmers, R.; Jenkins, R., Jr.; Turchi, I. J.; Watson, W. H.; Chen, J. S.; Kimura, M. J. Am. Chem. Soc. 1980, 102, 2000.
10. Oxaziridine 4 was prepared by an improved procedure developed by Davis (Davis, F. A.; Stringer, O. D. J. Org. Chem. 1982, 47, 1774) with a slight modification in product isolation. In our hands, oxaziridine 4 could be obtained in high purity and good chemical yield (90%) by filtering the concentrated reaction mixture through flash silica gel to remove the phase-transfer catalyst. Complete experimental details are given in the supplementary material.
11. Half-ester-imide 5 was prepared from the corresponding half-ester-acid chloride (Aldrich) under standard conditions; see: Evans, D. A.; Bartroli, J.; Shih, T. L. J. Am. Chem. Soc. 1981, 103, 2127.
12. Still, W. C.; Kahn, M.; Mitra, A. J. Org. Chem. 1978, 43, 2923.
13. Davis, F. A.; Mancinelli, P. A.; Balasubramanian, K.; Nadir, U. K. J. Am. Chem. Soc. 1979, 101, 1044.
14. Dale, J. A.; Dull, D. L.; Mosher, H. S. J. Org. Chem. 1969, 34, 2543.