Reactions at Other Carbon-linked Groups

Deprotection of an A-(benzyloxycarbonyl)aziridine to the free aziridine was accomplished using a nonhydrogenolytic technique, as shown in Equation (45) 92JOC5813 . 

A-Acylaziridines can be deprotonated to yield enolates, which can participate in alkylations and aldol condensations 91TL2533, 94AG(E)599 . The aziridine ring was used as a chiral auxiliary, and good to excellent diastereoselectivity was obtained. Equation (47) shows an example of such an enolate alkylation. Quenching the enolate with an aldehyde produced a single syn aldol adduct. 

A-Phenylaziridines may be cleaved to the A-unsubstituted aziridines in good yield with ozone 78TL3ii9). The stable hemiaminal adducts of aziridines with aldehydes may react with amines to give aminals (A-(l-aminoalkyl)aziridines) B-83Mi 101-01). 

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