1,1-Cyclopropane aminoketones were efficiently synthesized in high yields by the tandem reaction of α-amino aryl ketones with vinyl sulfonium salts using DBU as the base in CH(2)Cl(2). This methodology was utilized to synthesize 2-benzoyl quinolines.
The first catalytic asymmetric pseudo five-component (AB(2)C(2) type) reaction is reported. A spirocyclic chiral phosphoric acid catalyzed one-pot multicomponent reaction of aromatic aldehydes, anilines and β-ketoesters and afforded highly functionalized enantioenriched tetrahydropyridines with high levels of stereocontrol.
SummaryA one-pot three-component synthesis of dihydropyrimidinones via a molecular iodine-catalyzed tandem reaction of simple readily available mono-substituted urea, alkylaldehyde, and arylaldehyde has been developed. The reaction proceeds with high chemo- and regioselectivity to give highly diverse dihydropyrimidinones in reasonable yields under mild reaction conditions. Moreover, the first catalytic enantioselective version of this reaction was also realized by using chiral spirocyclic SPINOL-phosphoric acids.
A chiral 1,1′‐spirobiindane‐7,7′‐diol phosphoric acid is successfully applied as catalyst for the asymmetric synthesis of tetrahydropyridines (IV) from ketoester (I), aldehydes (II), and anilines (III).
A General Access to 1,1-Cyclopropane Aminoketones and Their Conversion into 2-Benzoyl Quinolines. -A novel, direct synthesis of 1,1-cyclopropane aminoketones via base-mediated tandem reaction of α-amino ketones with vinyl sulfonium salts is developed. These cyclopropane aminoketones can be easily transformed into 2-benzoylquinolines via treatment with DEAD. -(MAO, Z.; QU, H.; ZHAO, Y.; LIN*, X.; Chem. Commun. (Cambridge) 48 (2012) 79, 9927-9929, http://dx.
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