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Issue 14, 2013
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Scope and limitations of diastereoselective aziridination reactions using stabilised ammonium ylides or α-bromo carbonyl nucleophiles

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Abstract

The applicability of easily available ammonium salts to access aziridines via an ammonium ylide pathway was carefully investigated and compared with classical aza-Darzens approaches using α-bromo carbonyl nucleophiles. Whereas amide-stabilised ammonium ylides could be successfully reacted with aromatic aldimines to obtain the corresponding trans-aziridines in good yields and with high diastereoselectivities, α-bromo amides failed. In sharp contrast, acetophenone-based ylides did not give any aziridines while in this specific case α-bromo acetophenone derivatives gave the corresponding cis-aziridines in high yields and with excellent diastereoselectivities under optimised conditions.

Graphical abstract: Scope and limitations of diastereoselective aziridination reactions using stabilised ammonium ylides or α-bromo carbonyl nucleophiles

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Supplementary files

Article information


Submitted
25 Jan 2013
Accepted
29 Jan 2013
First published
30 Jan 2013

RSC Adv., 2013,3, 4552-4557
Article type
Paper

Scope and limitations of diastereoselective aziridination reactions using stabilised ammonium ylides or α-bromo carbonyl nucleophiles

S. Aichhorn, G. N. Gururaja, M. Reisinger and M. Waser, RSC Adv., 2013, 3, 4552
DOI: 10.1039/C3RA40429C

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