title: Concise synthesis of (+)-allo-kainic acid via MgI2-mediated tandem aziridine ring opening-formal [3 + 2] cycloaddition.
abstract: 3-Methyl vinyl aziridine undergoes a mild MgI2-promoted S(N)2' ring opening and concomitant cyclization with fumarate Michael acceptors to give trisubstituted pyrrolidines. The process is efficient and highly diastereoselective. This methodology has been applied to a concise asymmetric synthesis of (+)-allo-kainic acid.
authors.affiliation: School of Chemistry, University of Bristol, Cantock's Close, Bristol, BS8 1TS, UK.
authors.forename: Giada
authors.initials: G
authors.lastname: Arena
authors.forename: C Chun
authors.initials: CC
authors.lastname: Chen
authors.forename: Daniele
authors.initials: D
authors.lastname: Leonori
authors.forename: Varinder K
authors.initials: VK
authors.lastname: Aggarwal
mesh_terms: D000497:Alloys / Q000138:chemical synthesis* / Q000737:chemistry; D001388:Aziridines / Q000737:chemistry*; D003500:Cyclization; D061565:Cycloaddition Reaction; D007608:Kainic Acid / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D011759:Pyrrolidines / Q000737:chemistry*; D013237:Stereoisomerism; D014753:Vinyl Compounds / Q000737:chemistry*
chemical_list: C585759:3-methyl vinyl aziridine; D000497:Alloys; D001388:Aziridines; D011759:Pyrrolidines; D014753:Vinyl Compounds; C033132:aziridine; D007608:Kainic Acid