The application of biocatalysis to the synthesis of chiral molecules is one of the greenest technologies for the replacement of chemical routes due to its environmentally benign reaction conditions and unparalleled chemo-, regio- and stereoselectivities. We have been interested in searching for carbonyl reductase enzymes and assessing their substrate specificity and stereoselectivity. We now re...

Lewis acidic indium(III) salts, in particular In(NTf(2))(3), effect the conversion of alpha-(omega'-alkynyl)-beta-ketoesters and omega-alkynyl-beta-ketoesters to the corresponding cyclic products in a manner known as the Conia-ene reaction. This reaction can lead to the creation of five- to fifteen-membered-ring carbocycles and heterocycles in good to excellent yields. The synthetic features of...

Systematic studies of reaction conditions and subsequent optimization led to the identification of important parameters for stereoselectivity in the asymmetric alpha-hydroxylation reaction of 1,3-ketoesters. Enantioselectivities of up to 98% can be achieved for cyclic substrates and 88% for acyclic ketoesters. Subsequently, the combination of cyclic/acyclic ketoester, catalyst, and oxidant was ...

A series of N-substituted 1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylate esters has been prepared in two steps from ethyl 2-(2-chloronicotinoyl)acetate. Treatment of the b-ketoester with N,N-dimethylformamide dimethyl acetal in N,N-dimethylformamide (DMF) gave a 95% yield of the 2-dimethylaminomethylene derivative. Subsequent reaction of this b-enaminone with primary amines in DMF at 120C fo...

A convenient method is disclosed for the synthesis of both 3-hydroxyisoquinolines and 2-hydroxy-1,4-naphthoquinones from beta-ketoesters using a one-pot aryne acyl-alkylation/condensation procedure. When performed in conjunction with a one-step method for the synthesis of the beta-ketoester substrates, this method provides a new route to these polyaromatic structures in only two steps from comm...