Asymmetric Syntheses of Three-Membered Heterocycles Using Chiral Amide-Based Ammonium Ylides
(2015) Organic & Biomolecular Chemistry — Vol. 13, p. 2092-2099 (2015)
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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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Pichler, M., Novacek, J., Robiette, R., Poscher, V., Himmelsbach, M., Monkowius, U., Müller, N., & Waser, M. (2015). Asymmetric Syntheses of Three-Membered Heterocycles Using Chiral Amide-Based Ammonium Ylides. Organic & Biomolecular Chemistry, 13, 2092-2099. https://doi.org/10.1039/C4OB02318H (Original work published 2015)