Enantioselective Construction of alpha-Quaternary Cyclic Carbonyl Compounds by Catalytic Asymmetric Allylic Alkylation
소속 :
연사 : Prof. Jimin Kim(Chonnam National University)
일시 : 2014-12-04 16:30 ~
장소 : Mok-Am Hall , Bldg. 500
-Abstract-
Recently, we developed a mild transformation combining mechanistic elements of the Ugi reaction and Houben-Hoesch cyclization. This interrupted Ugi reaction was proven useful for preparation of indoxyls and 3-aminoindoles. In addition, our interrupted Ugi reaction has been successfully implemented for the synthesis of methoxy mitragynine pseudoindoxyl.
The asymmetric construction of quaternary stereocenters is a topic of great interest in the organic chemistry community. Among the available methods that afford this motif, palladium-catalyzed decarboxylative allylic alkylation has proven particularly effective and, over the last decade, Stoltz group has pursued this strategy employing chiral phosphinooxazoline (PHOX) ligands. Recently, the group disclosed the highly enantioselective palladium-catalyzed decarboxylative allylic alkylation of readily available lactams and imides to form a number of 3,3-disubstituted pyrrolidinones, piperidinones, caprolactams and structurally related N-heterocyclic compounds. In addition, cyclobutanones were successfully implemented in the enantioselective allylic alkylation serving synthetic building blocks to access a variety of enantioenriched derivative compounds. In this seminar, the palladium-catalyzed asymmetric allylic alkylations in lactams, cyclic imides, and small rings such as cyclobutanones will be discussed.
Recently, we developed a mild transformation combining mechanistic elements of the Ugi reaction and Houben-Hoesch cyclization. This interrupted Ugi reaction was proven useful for preparation of indoxyls and 3-aminoindoles. In addition, our interrupted Ugi reaction has been successfully implemented for the synthesis of methoxy mitragynine pseudoindoxyl.
The asymmetric construction of quaternary stereocenters is a topic of great interest in the organic chemistry community. Among the available methods that afford this motif, palladium-catalyzed decarboxylative allylic alkylation has proven particularly effective and, over the last decade, Stoltz group has pursued this strategy employing chiral phosphinooxazoline (PHOX) ligands. Recently, the group disclosed the highly enantioselective palladium-catalyzed decarboxylative allylic alkylation of readily available lactams and imides to form a number of 3,3-disubstituted pyrrolidinones, piperidinones, caprolactams and structurally related N-heterocyclic compounds. In addition, cyclobutanones were successfully implemented in the enantioselective allylic alkylation serving synthetic building blocks to access a variety of enantioenriched derivative compounds. In this seminar, the palladium-catalyzed asymmetric allylic alkylations in lactams, cyclic imides, and small rings such as cyclobutanones will be discussed.
