Enantioselective Construction of alpha-Quaternary Cyclic Carbonyl Compounds by Catalytic Asymmetric Allylic Alkylation
Date : December 4, 2014 16:30 ~
Speaker : Prof. Jimin Kim(Chonnam National University)
Location : Mok-Am Hall, Buld. 500
-Abstract-
GRADUATE RESEARCH: DEVELOPMENT OF THE INTERRUPTED UGI REACTION AND ITS APPLICATION TO THE SYNTHESIS OF 11-METHOXY MITRAGYNINE PSEUDOINDOXYL
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.
POSTDOCTORAL RESEARCH: PALLADIUM-CATALYZE DECARBOXYLATIVE ALKYLATION OF CYCLIC IMIDES
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.
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