NDLI: 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 crystallogr

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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 crystallogr

Content Provider	Semantic Scholar
Author	Pichler, Mathias Novacek, Johanna Robiette, Raphaël Poscher, Vanessa Himmelsbach, Markus Monkowius, Uwe Mueller, Norbert Waser, Mario
Copyright Year	2015
Abstract	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.
Starting Page	2092
Ending Page	2099
Page Count	8
File Format	PDF HTM / HTML
DOI	10.1039/c4ob02318h
Alternate Webpage(s)	http://www.rsc.org/suppdata/ob/c4/c4ob02318h/c4ob02318h1.pdf
Alternate Webpage(s)	https://pubs.rsc.org/en/content/articlepdf/2014/ob/c4ob02318h?page=search
Alternate Webpage(s)	http://pubs.rsc.org/en/content/articlepdf/2014/ob/c4ob02318h?page=search
Alternate Webpage(s)	http://pubs.rsc.org/en/content/articlepdf/2015/ob/c4ob02318h
Alternate Webpage(s)	http://pubs.rsc.org/en/content/getauthorversionpdf/C4OB02318H
PubMed reference number	25521410
Alternate Webpage(s)	https://doi.org/10.1039/c4ob02318h
Volume Number	13
Journal	Organic & biomolecular chemistry
Language	English
Access Restriction	Open
Content Type	Text
Resource Type	Article

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