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cis-Selective aziridination of cis- or trans-α,β-unsaturated amides using diaziridine

✍ Scribed by Kiyoto Hori; Hiroyasu Sugihar; Yoshio N. Ito; Tsutomu Katsuki

Book ID
104261722
Publisher
Elsevier Science
Year
1999
Tongue
French
Weight
219 KB
Volume
40
Category
Article
ISSN
0040-4039

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✦ Synopsis

Aziridination of (x,l~-unsamrated amides was effected by treatment with lithiated 3,3-pentamethylenediaziridine in high diastereoselectivity, c/s-Azin'dine was the predominant diastereomer irrespective of the geometry of the substrates. A stepwise mechanism, 1,4-addition of a lithiated diaziridine to o~,l~-unsaturated amides and subsequent ring closure at the nitrogen atom, was proposed to explain the unusual c/s-selectivity.

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