Issue 7, 2015

An improved procedure to prepare 3-methyl-4-nitroalkylenethylisoxazoles and their reaction under catalytic enantioselective Michael addition with nitromethane

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.

Graphical abstract: An improved procedure to prepare 3-methyl-4-nitroalkylenethylisoxazoles and their reaction under catalytic enantioselective Michael addition with nitromethane

Supplementary files

Article information

Article type
Paper
Submitted
03 Oct 2014
Accepted
02 Dec 2014
First published
02 Dec 2014

Org. Biomol. Chem., 2015,13, 2192-2195

Author version available

An improved procedure to prepare 3-methyl-4-nitroalkylenethylisoxazoles and their reaction under catalytic enantioselective Michael addition with nitromethane

M. Moccia, R. J. Wells and Mauro. F. A. Adamo, Org. Biomol. Chem., 2015, 13, 2192 DOI: 10.1039/C4OB02109F

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