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We speculate that the direct conversion of aziridine 2c into alkyne 4c is catalysed by unidentified species (e.g. organolithiums) that are not formed in the attempted conversion of vinyl ether 9 into alkyne 4c.
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16
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28944431629
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13 With N-Boc dihydropyrrole N-triisopropylbenzenesulfonyl aziridine, only reductive alkylation was observed even using sec-butyllithium and PMDETA.
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15 We have recently found that the α-lithiation-rearrangement of N-triisopropylbenzenesulfonyl-protected cyclopentene and cyclohexene aziridines using sec-butyllithium-(-)-sparteine to the corresponding allylic sulfonamides proceeds with the opposite sense of induction to the N-tosyl aziridines.
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