title: A stereoselective cyclization strategy for the preparation of γ-lactams and their use in the synthesis of α-methyl-β-proline.
abstract: A straightforward stereoselective and enantiodivergent cyclization strategy for the construction of γ-lactams is described. The cyclization strategy makes use of chiral malonic esters prepared from enantiomerically enriched monoesters of disubstituted malonic acid. The cyclization occurs with the selective displacement of a substituted benzyl alcohol as the leaving group. A Hammett study illustrates that the cyclization is under electronic control. The resulting γ-lactam can be readily converted into a novel proline analogue.
authors.affiliation: Department of Chemistry and Biochemistry, The University of Southern Mississippi, 118 College Drive No. 5043, Hattiesburg, Mississippi 39406, USA.
authors.forename: Souvik
authors.initials: S
authors.lastname: Banerjee
authors.forename: Justin
authors.initials: J
authors.lastname: Smith
authors.forename: Jillian
authors.initials: J
authors.lastname: Smith
authors.forename: Caleb
authors.initials: C
authors.lastname: Faulkner
authors.forename: Douglas S
authors.initials: DS
authors.lastname: Masterson
mesh_terms: D000596:Amino Acids / Q000737:chemistry*; D003500:Cyclization; D004952:Esters; D007769:Lactams / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D011392:Proline / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000596:Amino Acids; D004952:Esters; D007769:Lactams; C581651:alpha-methyl-beta-proline; D011392:Proline; C072401:beta-proline