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α‐Selective Organocatalytic Synthesis of 2‐Deoxygalactosides
Author(s) -
Balmond Edward I.,
Coe Diane M.,
Galan M. Carmen,
McGarrigle Eoghan M.
Publication year - 2012
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201204505
Subject(s) - moiety , thiourea , stereoselectivity , glycosylation , chemistry , organocatalysis , combinatorial chemistry , mechanism (biology) , stereochemistry , organic chemistry , catalysis , biochemistry , enantioselective synthesis , philosophy , epistemology
Alpha rules : A thiourea acts as an efficient organocatalyst for the glycosylation of protected galactals to form oligosaccharides containing a 2‐deoxymonosaccharide moiety (see scheme). The reaction is highly stereoselective for α‐linkages and proceeds by way of a syn ‐addition mechanism.
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