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Synlett 2011(14): 1978-1982  
DOI: 10.1055/s-0030-1261163
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Petasis Olefination in a Continuous-Flow Microwave Reactor: exo-Glycals from Sugar Lactones

Stefan Koch, Holger Löwe, Horst Kunz*
Institut für Organische Chemie, Johannes Gutenberg-Universität Mainz, Duesbergweg 10-14, 55128 Mainz, Germany
Fax: +49(6131)3924786; e-Mail: hokunz@uni-mainz.de;
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Publication History

Received 11 January 2011
Publication Date:
10 August 2011 (online)

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Abstract

An efficient Petasis olefination of sugar lactones under continuous-flow microwave conditions was developed. Their conversion into exo-glycals can be steered by adjusting the residence time and the concentration of the solution within the reactor. Applying a continuous-flow procedure, the reaction time can be shortened to less than three minutes, several hundred times shorter compared to values given in the literature for batch procedures. This setup is utilizable for a gram-scale synthesis of enol ethers and exo-glycals, in particular, such ones containing potentially (Lewis) acid sensitive acetalic protecting groups.

Key words

Petasis olefination - continuous-flow reactions - exo-glycals - sugar lactones - microwave support

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