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Lipase‐Mediated Synthesis of Both Enantiomers of Levoglucosenone from Acrolein Dimer
Author(s) -
Kadota Kohei,
Kurusu Takashi,
Taniguchi Takahiko,
Ogasawara Kunio
Publication year - 2001
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 - 10.1002/1615-4169(200108)343:6/7<618::aid-adsc618>3.0.co;2-e
Subject(s) - chemistry , enantiopure drug , acrolein , lipase , enantiomer , kinetic resolution , hydrolysis , dimer , chirality (physics) , organic chemistry , swern oxidation , enantiomeric excess , racemization , alcohol , enantioselective synthesis , enzyme , catalysis , dimethyl sulfoxide , chiral symmetry breaking , physics , quantum mechanics , quark , nambu–jona lasinio model
A synthesis of both enantiomers of levoglucosenone from acrolein dimer has been developed by employing lipase‐mediated kinetic hydrolysis. Thus, acrolein dimer is transformed into racemic dihydrolevoglucosenone by sequential hydride reduction, oxidative acetalization, and Swern oxidation. Employing Saegusa‐Larock conditions, dihydrolevoglucosenone is transformed into racemic levoglucosenone. The lipase‐mediated resolution was best carried out under hydrolysis conditions with the endo ‐acetate generated from racemic levoglucosenone to give rise to highly enantioenriched (+)‐alcohol and enantiopure (−)‐acetate serving as the precursors of enantiopure levoglucosenone having the corresponding chirality.