The asymmetric addition of phenylacetylene to aldehydes

Enantioselective formation of C-C bonds is an area of intense research.Among them, the asymmetric addition of alkynyl reagents to aldehydes is very useful for the synthesis of chiral secondary propargyl alcohols, which are very important building blocks for many chiral organic compounds, and the acetylene and hydroxyl founctional group of propargyl alcohol can be easily transfered into many other structures.1Recently, many significant chiral ligands have been disclosed.2 Here, we report our r…

The asymmetric addition of phenylacetylene to aldehydes

Enantioselective formation of C-C bonds is an area of intense research. Among them, the asymmetric addition of alkynyl reagents to aldehydes is very useful for the synthesis of chiral secondary propargyl alcohols, which are very important building blocks for many chiral organic compounds, and the acetylene and hydroxyl founctional group of propargyl alcohol can be easily transfered into many other structures.1Recently, many significant chiral ligands have been disclosed.2 Here, we report our research results in the asymmetric addition of phenylacetylene to aldehydes.We chose L-phenylalanine and camphor as starting materials, after simple steps, we got 1 and 2.Ligand 1 and 2 behave excellent catalytic activity for the reaction of enantioselective addition of phenylacetylene to aldehydes (the ee up to 98%) under very mild conditions.3,4L-Proline and its derivatives have become a series of important molecules in asymmetric catalysis due to its rigid structure, easy availability, and cheapness. We used commercial Boc-L-proline as chiral ligand in this reaction and get good result (up to 77% ee).5