Journal
ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 13, Issue 7, Pages 2092-2099Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c4ob02318h
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Funding
- Austrian Science Funds (FWF) [P26387-N28]
- Fond de la Recherche Scientifique de Belgique (F.R.S.-FNRS) [2.5020.11]
- European Union through the EFRE INTERREG IV ETC-AT-CZ program [M00146]
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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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