The Enantioselective Addition of Alkyne Nucleophiles to Carbonyl Groups

Enantioselective addition of organozinc reagents to carbonyl compounds*

Different chiral camphorsulfonamide derivatives containing a hydroxy or a sulfonamido functionality, as well as chiral 1,2-hydroxysulfonamides, have been evaluated as chiral promoters in the classical enantioselective addition of dialkylzinc reagents to aldehydes in the presence of titanium tetraisopropoxide (ee up to 96 %). Surprisingly, ligands with a structure of isoborneol are able to promo...

Enantioselective titanium-promoted 1,2-additions of carbon nucleophiles to carbonyl compounds

Copper-Catalyzed Enantioselective Addition of Styrene-Derived Nucleophiles to Imines Enabled by Ligand-Controlled Chemoselective Hydrocupration

The copper-catalyzed intermolecular enantioselective addition of styrenes to imines has been achieved under mild conditions at ambient temperature. This process features the use of styrenes as latent carbanion equivalents via the intermediacy of catalytically generated benzylcopper derivatives, providing an effective means for accessing highly enantiomerically enriched amines bearing contiguous...

Addition of silylated nucleophiles to α-oxoketenes.

A general evaluation of silylated nucleophiles to intercept transient α-oxoketenes generated by microwave-assisted Wolff rearrangement of 2-diazo-1,3-dicarbonyl compounds is presented. Original scaffolds and synthetic intermediates are accessed in a rapid, efficient and easy-to-handle way. Mechanistic studies by DFT calculations and some post-functionalizations are discussed.

Catalytic enantioselective addition to imines.

Chiral nitrogen-containing compounds are widely distributed in nature and include many biologically important molecules (Chart 1). In these compounds, the nitrogen-containing units are known to play important roles for their bioactivities. For the synthesis of these chiral nitrogen-containing building blocks, use of imines as electrophiles is the most promising and convenient route.1 While many...