N-silyl protecting groups for labile aziridines: Application toward the synthesis of N-H aziridinomitosenes

Don L. Warner, Amber M. Hibberd, Monica Kalman, Artis Klapars, Edwin Vedejs

Research output: Contribution to journalArticlepeer-review

18 Scopus citations

Abstract

(Chemical Equation Presented) Hindered N-silylamines were examined for their utility to serve as protecting groups for the labile aziridine nitrogen found within the highly sensitive aziridinomitosene framework. tert-Butyldiphenylsilyl and modified tert-butyldiphenylsilyl groups were the most resistant to nitrogen-silicon bond cleavage under various reaction conditions and were thus employed in transformations relevant to aziridinomitosene synthesis. The N-silylaziridines 7a, 21a, and 21b underwent azomethine ylide cycloaddition and afforded, upon deprotection, the N-H aziridine 24 in 18-32% overall yield for the three steps.

Original languageEnglish
Pages (from-to)8519-8522
Number of pages4
JournalJournal of Organic Chemistry
Volume72
Issue number22
DOIs
StatePublished - 26 Oct 2007

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