The chemistry of cyclopropanols

Over the past five years, several metal-catalyzed asymmetric ring-cleaving reactions have been developed that generate ring-opened products in high yield and enantiomeric excess. These reactions can be carried out with a range of nucleophiles including hydride, stabilized and nonstabilized carbanions, alcohols, amines, and carboxylates. To achieve these results, three different transition metals have been employed, namely nickel, palladium, and rhodium, leading not only to synthetically useful transformations but also to a greater understanding of the reaction manifolds possible with these metals. This Account covers the work by our group and by others toward the development of new metal-catalyzed asymmetric ring-opening reactions of oxabicyclic alkenes.

Transition metal-catalyzed enantioselective ring-opening reactions of oxabicyclic alkenes.

Enantioselective synthesis through enzymatic asymmetrization

Enzymes in the synthesis of chiral drugs.

Nichtlineare Effekte bei asymmetrischen Synthesen und stereoselektiven Reaktionen

Stereoselective pig liver esterase-catalyzed hydrolysis of rigid bicyclic meso-diesters: preparation of optically pure 4,7-epoxytetra- and hexa-hydrophthalides

Enzymatic resolution of methyl 2-alkyl-2-arylacetates

La cyclopropanation des ethers d'enol trimethylsilyliques, mode de preparation des cyclopropanols et methode d'α-monomethylation des aldehydes et des cetones.

The cyclopropanation of silyl enol ethers of cisoid or labile α-ethylenic ketones. A general and rapid route to cyclobutanones and cyclopentanones.

1,2-Anti diastereoselective reduction of 2-alkyl-3-hydroxy-ketones via their silyl ethers

C. Girard

Papers

Stereoselective pig liver esterase-catalyzed hydrolysis of rigid bicyclic meso-diesters: preparation of optically pure 4,7-epoxytetra- and hexa-hydrophthalides

Enzymatic resolution of methyl 2-alkyl-2-arylacetates

La cyclopropanation des ethers d'enol trimethylsilyliques, mode de preparation des cyclopropanols et methode d'α-monomethylation des aldehydes et des cetones.

The cyclopropanation of silyl enol ethers of cisoid or labile α-ethylenic ketones. A general and rapid route to cyclobutanones and cyclopentanones.

1,2-Anti diastereoselective reduction of 2-alkyl-3-hydroxy-ketones via their silyl ethers