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Short and simple synthesis of (R)‐ and (S)‐4‐hydroxypentylaminoacetamide : both enantiomers of the (ω‐1)‐hydroxylated metabolite of milacemide
Author(s) -
Gorissen Hugo J.,
Van Hoeck JeanPierre,
Mockel Anne M.,
Journée Guido H.,
Delatour Claude,
Libert Valéry R.
Publication year - 1992
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.530040505
Subject(s) - chemistry , enantiomer , kinetic resolution , metabolite , reductive amination , stereochemistry , enantiomeric excess , lipase , pancreatic lipase , enantioselective synthesis , organic chemistry , enzyme , catalysis , biochemistry
Both (R)‐ and (S)‐4‐hydroxypentylaminoacetamide have been synthesized by reductive amination of glycinamide on the γ‐valerolactols corresponding to (R)‐ and (S)‐γ‐valerolactone, respectively. These enantiomeric lactones were readily obtained in high enantiomeric excess (ee) by enzymic porcine pancreatic lipase (PPL) kinetic resolution of rac ‐methyl γ‐hydroxyvalerate. © 1992 Wiley‐Liss, Inc.