title: Diastereoselective synthesis of γ- and δ-lactams from imines and sulfone-substituted anhydrides.
abstract: Sulfone-substituted γ- and δ-lactams have been prepared in a single step with high diastereoselectivity. Sulfonylglutaric anhydrides produce intermediates that readily decarboxylate to provide δ-lactams with high diastereoselectivity. Substituents at the 3- or 4-position of the glutaric anhydride induce high levels of stereocontrol. Sulfonylsuccinic anhydrides produce intermediate carboxylic acids that can be trapped as methyl esters or allowed to decarboxylate under mild conditions. This method has been applied to a short synthesis of the pyrrolizidine alkaloid (±)-isoretronecanol.
authors.affiliation: Department of Chemistry, University of California, Davis , One Shields Avenue, Davis, California 95616, United States.
authors.forename: Nohemy A
authors.initials: NA
authors.lastname: Sorto
authors.forename: Michael J
authors.initials: MJ
authors.lastname: Di Maso
authors.forename: Manuel A
authors.initials: MA
authors.lastname: Muñoz
authors.forename: Ryan J
authors.initials: RJ
authors.lastname: Dougherty
authors.forename: James C
authors.initials: JC
authors.lastname: Fettinger
authors.forename: Jared T
authors.initials: JT
authors.lastname: Shaw
mesh_terms: D000812:Anhydrides; D007097:Imines / Q000737:chemistry*; D007769:Lactams / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D011763:Pyrrolizidine Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D013450:Sulfones / Q000737:chemistry*
chemical_list: D000812:Anhydrides; D007097:Imines; D007769:Lactams; D011763:Pyrrolizidine Alkaloids; D013450:Sulfones; C051740:isoretronecanol