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Benzylic Ammonium Ylide Mediated Epoxidations.

ABSTRACT: A high yielding synthesis of stilbene oxides using ammonium ylides has been developed. It turned out that the amine leaving group plays a crucial role as trimethylamine gives higher yields than DABCO or quinuclidine. The amine group also influences the diastereoselectivity, and detailed DFT calculations to understand the key parameters of these reactions have been carried out.

SUBMITTER: Roiser L

PROVIDER: S-EPMC5068558 | biostudies-literature | 2016 Aug

REPOSITORIES: biostudies-literature

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Benzylic Ammonium Ylide Mediated Epoxidations.

Roiser Lukas L Robiette Raphaël R Waser Mario M

Synlett : accounts and rapid communications in synthetic organic chemistry 20160615 13

A high yielding synthesis of stilbene oxides using ammonium ylides has been developed. It turned out that the amine leaving group plays a crucial role as trimethylamine gives higher yields than DABCO or quinuclidine. The amine group also influences the diastereoselectivity, and detailed DFT calculations to understand the key parameters of these reactions have been carried out. ...[more]

PMID: 27766017

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