title: A microwave-assisted synthesis of (S)-N-protected homoserine γ-lactones from L-aspartic acid.
abstract: A three-pot preparation of (S)-N-protected homoserine γ-lactones is presented. Conversion of N-protected L-aspartic acid to an oxazolidinone is followed by selective reduction/acid-catalyzed cyclization to deliver the lactones. Microwave irradiation proved valuable for improving the latter reaction steps in some cases.
authors.affiliation: Department of Chemistry, University of Guelph, Guelph, Ontario, Canada N1G 2W1.
authors.forename: Suneel P
authors.initials: SP
authors.lastname: Singh
authors.forename: Alex
authors.initials: A
authors.lastname: Michaelides
authors.forename: A Rod
authors.initials: AR
authors.lastname: Merrill
authors.forename: Adrian L
authors.initials: AL
authors.lastname: Schwan
mesh_terms: D015107:4-Butyrolactone / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D001224:Aspartic Acid / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D008872:Microwaves; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: C088386:homoserine lactone; D001224:Aspartic Acid; D015107:4-Butyrolactone