Abstract
In this study, the highly strained three-membered aziridine ring was successfully activated as the aziridinium ion by alkylation of the ring nitrogen with a methyl, ethyl or allyl group, which was followed by ring opening with external nucleophiles such as acetate and azide. Such alkylative aziridine ring opening provides an easy route for the synthesis of various N-alkylated amine-containing molecules with concomitant introduction of an external nucleophile at either its α- or β-position.
Highlights
IntroductionA nitrogen-containing three-membered three-membered ring, ring, has has high high ring strain similar to oxirane and cyclopropane [1,2,3,4,5,6,7,8,9,10,11,12]
We found the(4allylative aziridinium ion was able to be generated with based on the starting substrates: A, R = CH2 OBn; B, R = CH2 OTES; C, R = CH2 OTBS; ICH2CHCH2 (1.25 equiv.), AgOTf (1.05 equiv.) in CH3CN and external nucleophiles for
We found that the allylative aziridinium ion was able to be generated with ICH2 CHCH2 (1.25 equiv.), AgOTf (1.05 equiv.) in CH3 CN and external nucleophiles for ring opening (Table 2)
Summary
A nitrogen-containing three-membered three-membered ring, ring, has has high high ring strain similar to oxirane and cyclopropane [1,2,3,4,5,6,7,8,9,10,11,12]. The non-activated non-activated aziridine-bearing aziridine-bearing electron donating group at the ring nitrogen is relatively stable and inert toward almost all nucleophiles. It should should be be activated activated properly properly as an aziridinium ion or its equivalent prior to ring-opening reaction, as shown in Scheme 1 [13,14]
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