title: AlCl3-promoted selective Michael addition with allenoate and methyleneindolinone: synthesis of spirocyclic oxindole by using allenoate as a four-carbon component building block.
abstract: The AlCl3-promoted cyclization of readily available allenoates with methyleneindolinone is disclosed. The present strategy provides a rapid access to spirocyclic oxindole-cyclohexenones in an efficient manner. Remarkably, the allenoate is implemented as a four-carbon (4C) component to form the ring, which shows high synthetic efficiency. Flexibility of this method allows quick synthesis of spirocyclic oxindole-dihydropyrans by varying one of the components. It is also noteworthy that AlCl3 serves as the chlorine source as well as an effective catalyst to facilitate this interesting transformation.
authors.affiliation: Department of Chemistry, Innovative Drug Research Center, Shanghai University , Shanghai 200444, China.
authors.forename: Shibo
authors.initials: S
authors.lastname: Xu
authors.forename: Chunju
authors.initials: C
authors.lastname: Li
authors.forename: Xueshun
authors.initials: X
authors.lastname: Jia
authors.forename: Jian
authors.initials: J
authors.lastname: Li
mesh_terms: D000077410:Aluminum Chloride; D017607:Aluminum Compounds / Q000737:chemistry*; D002244:Carbon / Q000737:chemistry*; D002384:Catalysis; D002712:Chlorides / Q000737:chemistry*; D003500:Cyclization; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D000078183:Oxindoles; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D017607:Aluminum Compounds; D002712:Chlorides; D007211:Indoles; D000078183:Oxindoles; D013141:Spiro Compounds; C022960:2-oxindole; D000077410:Aluminum Chloride; D002244:Carbon