title: Tandem Prins/Wagner/Ritter process for the stereoselective synthesis of (3-oxabicyclo[4.2.0]octanyl)amide and (1-(5-aryltetrahydrofuran-3-yl)cyclobutyl)amide derivatives.
abstract: Three-component coupling of aldehydes, vinylcyclopropyl carbinols, and nitriles in the presence of 10 mol% TMSOTf at -40 to 0 °C in dichloromethane affords a novel class of (3-oxabicyclo[4.2.0]octanyl)amides in high yields with excellent selectivity, whereas (1-vinylcyclobutyl)methanol provides the corresponding (1-(5-aryltetrahydrofuran-3-yl)cyclobutyl)amides under similar conditions. This is the first report on the synthesis of oxabicycles through a sequential Prins/Wagner/Ritter process.
authors: Natural Product Chemistry, CSIR-Indian Institute of Chemical Technology, Hyderabad-500 007, India. basireddy@iict.res.in.
authors: B V
authors: BV
authors: Subba Reddy
authors: K
authors: K
authors: Muralikrishna
authors: J S
authors: JS
authors: Yadav
authors: N
authors: N
authors: Jagdeesh Babu
authors: K
authors: K
authors: Sirisha
authors: A V S
authors: AV
authors: Sarma
mesh_terms: D000577:Amides / Q000138:chemical synthesis* / Q000737:chemistry; D001688:Biological Products / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D002384:Catalysis; D002625:Chemistry, Organic / Q000379:methods*; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D008968:Molecular Conformation; D017550:Spectroscopy, Fourier Transform Infrared; D013237:Stereoisomerism
chemical_list: D000577:Amides; D001688:Biological Products; D005663:Furans