Synthesis of Chromanes through RCM–Transfer Hydrogenation

Bernd Schmidt; Stefan Krehl; Veronica Sotelo-Meza

doi:10.1055/s-0031-1289758

Synthesis, Table of Contents

Synthesis 2012; 44(11): 1603-1613
DOI: 10.1055/s-0031-1289758

feature article

Synthesis of Chromanes through RCM–Transfer Hydrogenation

Bernd Schmidt*

Universitaet Potsdam, Institut fuer Chemie (Organische Synthesechemie), Karl-Liebknecht-Straße 24-25, 14476 Potsdam-Golm, Germany, Fax: +49(331)9775059 Email: bernd.schmidt@uni-potsdam.de

,

Stefan Krehl

Universitaet Potsdam, Institut fuer Chemie (Organische Synthesechemie), Karl-Liebknecht-Straße 24-25, 14476 Potsdam-Golm, Germany, Fax: +49(331)9775059 Email: bernd.schmidt@uni-potsdam.de

,

Veronica Sotelo-Meza

Universitaet Potsdam, Institut fuer Chemie (Organische Synthesechemie), Karl-Liebknecht-Straße 24-25, 14476 Potsdam-Golm, Germany, Fax: +49(331)9775059 Email: bernd.schmidt@uni-potsdam.de

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Abstract

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Abstract

A sequential ruthenium-catalyzed ring-closing metathesis–transfer hydrogenation sequence has been established as a synthesis of chromanes starting from 2-(allyloxy)styrenes. The sequence requires only one precatalyst, the first-generation Grubbs catalyst, which is converted into a ruthenium hydride species in situ. Propan-2-ol serves as a chemical trigger for the formation of the ruthenium hydride and as hydrogen source.

Key words

ruthenium - chromanes - tandem reactions - metathesis - styrenes

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References

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