1009643-83-7Relevant academic research and scientific papers
Enantioselective synthesis of gabapentin analogues via organocatalytic asymmetric Michael addition of α-branched aldehydes to β-nitroacrylates
Yoshida, Masanori,Masaki, Erika,Ikehara, Hiroto,Hara, Shoji
experimental part, p. 5289 - 5297 (2012/08/08)
Michael addition reaction of α-branched aldehydes to β-nitroacrylates was successfully carried out by using a mixed catalyst consisting of a primary amino acid, l-phenylalanine, and its lithium salt to give β-formyl-β′-nitroesters having a quaternary carbon centre in good yields (up to 85%) with high enantioselectivity (up to 98% ee). By using benzyl β-nitroacrylates as Michael acceptors, the obtained β-formyl-β′-nitroesters were converted into various 4,4-disubstituted pyrrolidine-3-carboxylic acids including analogues of gabapentin (Neurotin) in one step from the Michael adducts in high yields. The Royal Society of Chemistry 2012.
Highly efficient catalytic system for enantioselective Michael addition of aldehydes to nitroalkenes in water
Zhu, Shaolin,Yu, Shouyun,Ma, Dawei
, p. 545 - 548 (2008/09/21)
(Chemical Equation Presented) Organocatalysis: A highly effective catalytic procedure for the Michael addition of aldehydes to nitroalkenes is achieved by combining the excellent asymmetric induction ability of o-TMS-protected diphenylprolinol compounds, the quick formation of enamines in the presence of benzoic acid, and the highly concentrated organic phase in water (see scheme; TMS=trimethylsilyl).
