An improved procedure to prepare 3-methyl-4-nitroalkylenethylisoxazoles and their reaction under catalytic enantioselective Michael addition with nitromethane. Issue 7 (2nd January 2015)

• Record Type: Journal Article
• Authors: Moccia, Maria; Wells, Robert J.; Adamo, Mauro. F. A.
• Is Part Of: Organic & biomolecular chemistry. Volume 13:Issue 7(2015)
• Page Start: 2192
• Page End: 2195
• Publication Date: 2015-01-02
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/c4ob02109f
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : A two-step preparation of 3-methyl-4-nitro-5-alkylethenyl isoxazoles is herein reported. These were reacted with nitromethane under phase-transfer catalysis to provide highly enantioenriched adducts (up to 93% ee). Abstract : Herein, we describe a short synthesis of 3-methyl-4-nitro-5-alkylethenyl isoxazoles and their reactivity as Michael acceptors. The title compounds reacted with nitromethane under phase-transfer catalysis to provide highly enantioenriched adducts (up to 93% ee) which were then converted to the corresponding γ-nitroacids.