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Asymmetric synthesis of δ ‐lactones with lipase catalyst
Author(s) -
Shimotori Yasutaka,
Sekine Kazuki,
Miyakoshi Tetsuo
Publication year - 2007
Publication title -
flavour and fragrance journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.393
H-Index - 70
eISSN - 1099-1026
pISSN - 0882-5734
DOI - 10.1002/ffj.1836
Subject(s) - chemistry , acetylation , enantiomer , lipase , hydrolysis , catalysis , triacylglycerol lipase , enantioselective synthesis , pancreatic lipase , enantiomeric excess , organic chemistry , stereochemistry , enzyme , biochemistry , gene
Both enantiomers of δ ‐lactones ( δ ‐decalactone, δ ‐undecalactone and δ ‐dodecalactone) were synthesized in three steps via Novozym 435‐catalysed acetylation of rac ‐ N ‐methyl‐5‐hydroxyalkylamides with about 80% e.e. The enantiomeric excess of δ ‐lactones was increased to 89–99% e.e. by substitution of porcine pancreatic lipase (PPL)‐catalysed hydrolysis of rac ‐ N ‐methyl‐5‐acetoxyalkylamides for Novozym 435‐catalysed acetylation of rac ‐ N ‐methyl‐5‐hydroxyalkylamides. Copyright © 2007 John Wiley & Sons, Ltd.