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Synthesis of Pyranoid and Furanoid Glycals from Glycosyl Sulfoxides by Treatment with Organolithium Reagents
Author(s) -
Gómez Ana M.,
Casillas Marta,
Barrio Aitor,
Gawel Anna,
López J. Cristóbal
Publication year - 2008
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.200800318
Subject(s) - chemistry , glycosyl , glycal , reagent , sulfoxide , substituent , derivative (finance) , organic chemistry , combinatorial chemistry , catalysis , stereoselectivity , financial economics , economics
Glycosyl sulfoxides can be conveniently transformed into pyranoid or furanoid glycals by treatment with organolithium reagents. The more likely reaction pathway involves a sulfoxide/metal exchange reaction to generate a glycosyllithium derivative that undergoes β‐elimination of its C‐2 substituent. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)