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Synthesis of Methoxy‐Substituted Exocyclic ( E )‐ and ( Z )‐Unsaturated Methyl Pyranosides and a Study of Their Reactivity towards Lewis Acids
Author(s) -
Deleuze Aurélie,
Sollogoub Matthieu,
Blériot Yves,
Marrot Jérôme,
Sinaÿ Pierre
Publication year - 2003
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200300105
Subject(s) - chemistry , enol , reactivity (psychology) , lewis acids and bases , derivative (finance) , enol ether , double bond , stereochemistry , organic chemistry , medicinal chemistry , catalysis , medicine , alternative medicine , pathology , financial economics , economics
The first synthesis of methoxy‐substituted exocyclic ( E )‐ and ( Z )‐unsaturated methyl pyranosides is reported involving the syn elimination of a selenoxide derivative as a key step. The rearrangement of these exocyclic enol ethers in the presence of TIBAL and DIBAL‐H is also described. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)