6533b82efe1ef96bd1293d3d
RESEARCH PRODUCT
Asymmetric Intramolecular Aza-Michael Reaction in Desymmetrization Processes. Total Synthesis of Hippodamine and epi-Hippodamine
María Sánchez-rosellóSantos FusteroMarta GuerolaCristina MuletCarlos Del Pozosubject
Natural productStereochemistryOrganic ChemistryTotal synthesisHippodamineBiochemistryDesymmetrizationchemistry.chemical_compoundchemistryNucleophileIntramolecular forceMichael reactionMoleculePhysical and Theoretical Chemistrydescription
The use of chiral sulfinyl amines both as nucleophilic nitrogen sources and chiral inducers has been described for the first time in a desymmetrization-type process involving an intramolecular aza-Michael reaction. The resulting product was employed as an advanced intermediate in the total synthesis of the natural product hippodamine and epi-hippodamine, taking advantage of the special symmetry of these molecules. In addition, this is the first asymmetric total synthesis of epi-hippodamine.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2015-01-01 | Organic Letters |