title: Synthesis of cis-octahydroindoles via intramolecular 1,3-dipolar cycloaddition of 2-acyl-5-aminooxazolium salts.
abstract: A concise method for the diastereoselective synthesis of octahydroindoles is presented. The products contain 2-amido and 7-hydroxyl substituents. A series of 2-acyl-5-aminooxazoles were prepared in one step. Upon methylation of the oxazole nitrogen atom, the substrates underwent rapid intramolecular 1,3-dipolar cycloaddition with a tethered alkene and, after reduction with excess hydride, produced octahydroindoles with excellent diastereoselectivity. The method allows for the installation of α-quaternary stereogenic carbon atoms.
authors.affiliation: Department of Chemistry, Henson School of Science and Technology, Salisbury University, 1101 Camden Avenue, Salisbury, Maryland 21801, USA.
authors.forename: Corey H
authors.initials: CH
authors.lastname: Basch
authors.forename: Jameson A
authors.initials: JA
authors.lastname: Brinck
authors.forename: Joaquin E
authors.initials: JE
authors.lastname: Ramos
authors.forename: Stephen A
authors.initials: SA
authors.lastname: Habay
authors.forename: Glenn P A
authors.initials: GP
authors.lastname: Yap
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D003500:Cyclization; D061565:Cycloaddition Reaction; D008745:Methylation; D010080:Oxazoles / Q000138:chemical synthesis* / Q000737:chemistry; D012492:Salts / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000475:Alkenes; D010080:Oxazoles; D012492:Salts