Regioselectivity in nucleophilic ring-opening of aziridinones

Abstract

The proportions of products derived from competing modes of ring-opening of 1,3-di-tert-butylaziridinone and similar aziridinones by a variety of nitrogen, oxygen, sulfur and halogen nucleophiles do not agree with simple guidelines postulated in the literature for these types of aziridinones.

References

1. I. Lengyel and J. C. Sheehan, Angew. Chem., Int. Ed. Engl., 1968, 25.
2. G. L'abbe, Angew. Chem., Int. Ed. Engl., 1980, 276.
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5. E. R. Talaty, M. M. Yusoff, S. A. Ismail, J. A. Gomez, C. E. Keller and J. M. Younger, Synlett, 1997, 6, 683.
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8. H. Quast and H. Leybach, Chem. Ber., 1991, 124, 2105 also studied this reaction.
9. R. V. Hoffman, N. K. Nayyar and W. Chen, J. Org. Chem., 1995, 60, 4121 have relied exclusively on Scheme 1 to explain products arising from an aziridinone involved as an intermediate (R¹= Ph or CO₂Et, R²= Me) and have correlated products with nucleophilic constants. However, in no case was the aziridinone actually isolated H. E. Baumgarten, J. F. Fuerholzer, R. D. Clark and R. D. Thompson, J. Am. Chem. Soc., 1963, 85, 3303; S. Sarel, B. A. Weissman and Y. Stein, Tetrahedron Lett., 1971, 373 studied the reaction of KOBu^t, MeOH or Bu^tOH with 1-tert-butyl-3-phenylaziridinone and 1-tert-butyl-3-bis-norcholanylaziridinone, respectively, the results being in accord with the simple guidelines (refs. 1 and 2).
10. Second and third reactions: work done by S. A. Ismail in our laboratory.