| Autor: |
Sun AW; Warren and Katherine Schlinger Laboratory for Chemistry and Chemical Engineering , Division of Chemistry and Chemical Engineering , California Institute of Technology , Pasadena , California 91125 , USA . Email: stoltz@caltech.edu., Hess SN; Warren and Katherine Schlinger Laboratory for Chemistry and Chemical Engineering , Division of Chemistry and Chemical Engineering , California Institute of Technology , Pasadena , California 91125 , USA . Email: stoltz@caltech.edu., Stoltz BM; Warren and Katherine Schlinger Laboratory for Chemistry and Chemical Engineering , Division of Chemistry and Chemical Engineering , California Institute of Technology , Pasadena , California 91125 , USA . Email: stoltz@caltech.edu. |
| Abstrakt: |
An enantioselective synthesis of diverse N 4-Boc-protected α,α-disubstituted piperazin-2-ones using the palladium-catalyzed decarboxylative allylic alkylation reaction has been achieved. Using a chiral Pd-catalyst derived from an electron deficient PHOX ligand, chiral piperazinones are synthesized in high yields and enantioselectivity. The chiral piperazinone products can be deprotected and reduced to valuable gem -disubstituted piperazines. This reaction is further extended to enable the enantioselective synthesis of α,α-disubstituted tetrahydropyrimidin-2-ones, which are hydrolyzed into corresponding chiral β 2,2 -amino acids. |
