Biomimetic Organocatalytic Asymmetric Synthesis of 2-Substituted Piperidine-Type Alkaloids and Their Analogues

Natural substances such as pelletierine and its analogues have been prepared in up to 97% ee and good yield by a protective-group-free, biomimetic approach. Usage of benzonitrile or acetonitrile as solvents effectively prevents product racemization

Unsaturated beta-ketoesters as versatile electrophiles in organocatalysis

beta-Ketoesters, which have widely been employed as nucleophiles, are also useful electrophiles in organocatalytic quinine mediated cascade reactions, leading to the formation of products bearing multiple stereocenters in high stereoselectivity

Synergic asymmetric organocatalysis (SAOc) of Cinchona alkaloids and secondary amines in the synthesis of bicyclo[2.2.2]octan-2-ones

A synergistic effect between chiral secondary and tertiary amines gives access to bicyclo[2.2.2]octan-2-ones with up to 90% ee and >10: 1 dr. © The Royal Society of Chemistry

Enamine-Mediated Addition of Aldehydes to Cyclic Enones

The O-trimethylsilylated alpha,alpha-diphenyl-prolinol-catalyzed addition of aldehydes to cyclic unsaturated enones is described. The apparently unusual stereochemical outcome is discussed

The Rabe amination after a century: Direct addition of N-heterocycles to carbonyl compounds

A catalytic version of the Rabe electrophilic amination is presented. This kind of reaction was originally employed in 1918 in a key step for the conversion of quinotoxine to quinine. Ketones and α-substituted aldehydes give the corresponding α-aminated carbonyl compounds in moderate yield. α,α-Unsubstituted aldehydes give rise to amino ketones via a novel rearrangement. © 2012 The Royal Society of Chemistry

Enantioselective Aza-Michael Addition of Imides by Using an Integrated Strategy Involving the Synthesis of a Family of Multifunctional Catalysts, Usage of Multiple Catalysis, and Rational Design of Experiment

A challenging asymmetric reaction (aza-Michael addition of imides to enones) has been optimized through an integrated approach involving the synthesis of a family of organocatalysts, multiple catalysis (usage of additives), and finally with rational exploration of the chemical space by the application of the experiment design