title: Asymmetric synthesis of spiro-epoxyoxindoles by the catalytic Darzens reaction of isatins with phenacyl bromides.
abstract: The asymmetric Darzens reaction between phenacyl bromides and N-protected isatins was developed to synthesize potentially bioactive spiro-epoxyoxindoles. The optically active products were obtained in moderate to good yields and enantioselectivities catalyzed by chiral N,N'-dioxide-Co(acac)2 complexes. A retro-aldol process accompanying the ring-closure step was observed in the process. A chiral control step was determined to be the initial aldol addition.
authors.affiliation: Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University , Chengdu 610064, China.
authors.forename: Yulong
authors.initials: Y
authors.lastname: Kuang
authors.forename: Yan
authors.initials: Y
authors.lastname: Lu
authors.forename: Yu
authors.initials: Y
authors.lastname: Tang
authors.forename: Xiaohua
authors.initials: X
authors.lastname: Liu
authors.forename: Lili
authors.initials: L
authors.lastname: Lin
authors.forename: Xiaoming
authors.initials: X
authors.lastname: Feng
mesh_terms: D000098:Acetophenones / Q000737:chemistry*; D000447:Aldehydes / Q000737:chemistry; D002384:Catalysis; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry*; D007510:Isatin / Q000031:analogs & derivatives* / Q000737:chemistry*; D015394:Molecular Structure; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000098:Acetophenones; D000447:Aldehydes; D007211:Indoles; D013141:Spiro Compounds; C013190:phenacyl bromide; D007510:Isatin; C116609:3-hydroxybutanal