Asymmetric syntheses of three-membered heterocycles using chiral amide-based ammonium ylides† †Electronic supplementary information (ESI) available: Experimental and computational details, characterization of new compounds, and copies of NMR spectra. CCDC 1023711 and 1030561. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c4ob02318h Click here for additional data file. Click here for additional data file.
نویسندگان
چکیده
The use of carbonyl-stabilised ammonium ylides to access chiral glycidic amides and the corresponding aziridines has so far been limited to racemic trans-selective protocols. We herein report the development of an asymmetric approach to access such compounds with high levels of stereoselectivity using easily accessible chiral auxiliary-based ammonium ylides. The use of phenylglycinol as the chiral auxiliary was found to be superior to Evans or pseudoephedrine-based auxiliaries resulting in good to excellent stereoselectivities in both, epoxidation and aziridination reactions.
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