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

ABSTRACT:

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.

Graphical abstract

SUBMITTER: Novacek J

PROVIDER: S-EPMC5225234 | biostudies-literature | 2017

REPOSITORIES: biostudies-literature

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

Novacek Johanna J Robiette Raphaël R Waser Mario M

Monatshefte fur chemie 20161124 1

<h4>Abstract</h4>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.<h4>Graphical abstract</h4> ...[more]

PMID: 28127093

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