title: Stereoselective synthesis of spiro[tetrahydropyran-3,3'-oxindole] derivatives employing Prins cascade strategy.
abstract: A variety of aldehydes undergo smooth coupling with 4-hydroxy-N-methyl-2-methylene-N-phenylbutanamide in the presence of BF3·OEt2 under ambient conditions to produce the corresponding spiro-oxindole derivatives in good yields with excellent selectivity. It is an entirely new strategy to construct the spirocycles in a one-pot operation through a Prins cascade process.
authors.affiliation: Natural Product Chemistry, ‡Centre for Chemical Biology, §Laboratory of Crystallography, and ⊥Centre for Nuclear Magnetic Resonance and Structural Chemistry, CSIR-Indian Institute of Chemical Technology , Tarnaka, Hyderabad 500 607, India.
authors.forename: B V Subba
authors.initials: BV
authors.lastname: Reddy
authors.forename: V
authors.initials: V
authors.lastname: Swathi
authors.forename: Manisha
authors.initials: M
authors.lastname: Swain
authors.forename: Manika Pal
authors.initials: MP
authors.lastname: Bhadra
authors.forename: B
authors.initials: B
authors.lastname: Sridhar
authors.forename: D
authors.initials: D
authors.lastname: Satyanarayana
authors.forename: B
authors.initials: B
authors.lastname: Jagadeesh
mesh_terms: D000447:Aldehydes / Q000737:chemistry*; D001880:Boranes / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D000078183:Oxindoles; D010654:Phenylbutyrates / Q000737:chemistry*; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: C000600314:4-hydroxy-N-methyl-2-methylene-N-phenylbutanamide; D000447:Aldehydes; D001880:Boranes; D007211:Indoles; D000078183:Oxindoles; D010654:Phenylbutyrates; D013141:Spiro Compounds; C000600312:spiro(tetrahydropyran-3,3'-oxindole); C022960:2-oxindole; C021274:boron trifluoride