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Aminals as Substrates for Sulfur Ylides:  A Synthesis of Functionalized Aziridines and N-Heterocycles

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journal contribution
posted on 24.05.2007, 00:00 by Christoforos G. Kokotos, Varinder K. Aggarwal
Sulfur ylides stabilized by Ar, vinyl, or amide groups react with five-membered-ring tert-butylsulfinyl aminals to give functionalized chiral, nonracemic aziridines in high yield and with good selectivities (up to 15:1 trans:cis, up to >95:5 trans dr, always >95:5 cis dr). The intermediate aziridines can be converted into pyrrolidines or piperidines depending on the reaction conditions.