On the origin of the stereoselectivity in chiral amide-based ammonium ylide-mediated epoxidations

Novacek, Johanna;Robiette, Raphaël;Waser, Mario
(2017) Monatshefte für Chemie : an international journal of chemistry — Vol. 148, n° 1, p. 77-81 (2017)

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Abstract
Detailed DFT studies provide an in-depth mechanistic understanding for the use of chiral amide-based ammonium ylides in epoxidation reactions. It is shown that the used chiral auxiliary efficiently shields one face of the ylide, which thus results in an extraordinarily high stereoselectivity giving only one trans-isomer with perfect control of the absolute configuration.
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Novacek, J., Robiette, R., & Waser, M. (2017). On the origin of the stereoselectivity in chiral amide-based ammonium ylide-mediated epoxidations. Monatshefte für Chemie : an international journal of chemistry, 148(1), 77-81. https://doi.org/10.1007/s00706-016-1866-8 (Original work published 2017)