Synthesis of Enantiomerically Pure Dihydrofurans and Dihydropyrans from Common Precursors Using RCM and Tandem RCM-Isomerization

Abstract Starting from glyceraldehyde, structurally and stereo­chemically diverse dihydrofurans and dihydropyrans with a 1,2-dihydroxyethylene side chain can be accessed in few steps via allyl metal addition, O-allylation and ring-closing metathesis (RCM) or tandem RCM-isomerization, respectively. T...

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Bibliographic Details
Published in:Synlett 2007-09, Vol.2007 (15), p.2375-2378
Main Authors: Schmidt, Bernd, Biernat, Anne
Format: Article
Language:English
Subjects:
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Summary:Abstract Starting from glyceraldehyde, structurally and stereo­chemically diverse dihydrofurans and dihydropyrans with a 1,2-dihydroxyethylene side chain can be accessed in few steps via allyl metal addition, O-allylation and ring-closing metathesis (RCM) or tandem RCM-isomerization, respectively. The synthesis of di­hydrofurans requires a selective double-bond isomerization on the homoallylic alcohol stage, prior to O-allylation and RCM or RCM-isomerization.
ISSN:0936-5214
1437-2096
DOI:10.1055/s-2007-985606