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Synthesis of Dihydrofurans and Dihydropyrans with Unsaturated Side Chains Based on Ring Size‐Selective Ring‐Closing Metathesis
Author(s) -
Schmidt Bernd,
Nave Stefan
Publication year - 2007
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.200600473
Subject(s) - enantiopure drug , chemistry , ring closing metathesis , metathesis , side chain , allylic rearrangement , salt metathesis reaction , ring size , ring (chemistry) , stereochemistry , selectivity , diol , enantioselective synthesis , catalysis , organic chemistry , polymerization , polymer
Enantiomerically pure 1,5‐hexadiene‐3,4‐diol, derived from D ‐mannitol in a few steps, may serve as a starting material for enantiopure dihydropyrans and dihydrofurans bearing an unsaturated side chain which is amenable for further synthetic transformations. The synthesis relies on a ring size‐selective ring‐closing metathesis reaction of a triene. Most likely, a catalyst‐directing effect of an allylic hydroxy group is responsible for the selectivity.