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Highly Selective Aziridination of Imines Using Trimethylsilyldiazomethane and Applications of C-Silylaziridines in Synthesis

Varinder K. Aggarwal and Marco Ferrara

*Department of Chemistry, University of Sheffield, Sheffield S3 7HF, U.K., Email:

V. K. Aggarwal, M. Ferrara, Org. Lett., 2000, 2, 4107-4110.

DOI: 10.1021/ol006772h

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The reaction of trimethylsilyldiazomethane with N-sulfonyl (Ts and SES) imines provides aziridines in good yields and high cis stereoselectivities. The silyl group can be substituted by treatment with a fluoride source and electrophiles again with high selectivity. In addition, complete regioselectivity is observed in ring opening reactions of these aziridines with nucleophiles.

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Key Words


ID: J54-Y2000