Synthesis 2012; 44(11): 1603-1613
DOI: 10.1055/s-0031-1289758
feature article
© Georg Thieme Verlag Stuttgart · New York

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
› Author Affiliations
Further Information

Publication History

Received: 02 March 2012

Received after revision: 23 March 2012

Publication Date:
24 April 2012 (online)


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.

Supporting Information