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Desymmetrization of meso ‐Glycerol Derivatives Induced by L ‐Histidine‐Derived Acylation Catalysts
Author(s) -
Sakakura Akira,
Umemura Shuhei,
Ishihara Kazuaki
Publication year - 2011
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.201100252
Subject(s) - desymmetrization , chemistry , acylation , bifunctional , enantioselective synthesis , catalysis , glycerol , histidine , organic chemistry , organocatalysis , combinatorial chemistry , enzyme
The desymmetrization of meso ‐glycerol derivatives bearing a 3‐pyrroline‐1‐carbonyl (Pyroc) directing group is demonstrated through an enantioselective acylation reaction promoted by L ‐histidine‐derived bifunctional catalysts. The desired monoacylated products are obtained in good yields (up to 74%) with high enantioselectivities (up to 99% ee ).