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 language | English |
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Pages (from-to) | 8519-8522 |
Number of pages | 4 |
Journal | Journal of Organic Chemistry |
Volume | 72 |
Issue number | 22 |
DOIs | |
State | Published - 26 Oct 2007 |