Highly Diastereo??and Enantioselective Aziridination of α, β??Unsaturated Amides with Diaziridine and Mechanistic Consideration on Its Stereochemistry

H Ishihara, K Hori, H Sugihara, YN Ito…

Index: Ishihara, Hiroyuki; Hori, Kiyoto; Sugihara, Hiroyasu; Ito, Yoshio N.; Katsuki, Tsutomu Helvetica Chimica Acta, 2002 , vol. 85, # 12 p. 4272 - 4286

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Citation Number: 18

Abstract

Abstract During studies of aziridination of α, β-unsaturated amides with diaziridine, we found that we could prepare both the cis-and trans-aziridinecarboxamides by choosing an appropriately substituted diaziridine. While 3-monosubstituted diaziridine 2 was suitable for the trans-selective aziridination, employment of 3, 3-dialkyldiaziridine 1 resulted in the formation of cis-aziridine carboxamides, irrespective of the geometry of the substrate ( ...