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Stereochemical Control of the Passerini Peter R. Andreana, Chang C. Liu, and Stuart L. Schreiber*

Summary: Stereochemical Control of the Passerini
Peter R. Andreana, Chang C. Liu, and Stuart L. Schreiber*
Howard Hughes Medical Institute, Center for Chemical Methodology and Library
DeVelopment (CMLD-HU) & Broad Institute of HarVard and MIT, Department of
Chemistry and Chemical Biology, HarVard UniVersity,
Cambridge, Massachusetts 02138
Received August 26, 2004
A catalytic asymmetric Passerini reaction using tridentate indan (pybox) Cu(II) Lewis acid complex 4 with substrates capable of bidentate
coordination has been achieved. The reaction occurs via ligand-accelerated catalysis.
Strategies, reagents, and catalysts that enable systematic
stereochemical and skeletal variation are central to effective
diversity-oriented syntheses (DOS).1-4 The Passerini three-
component coupling reaction (P-3CCR) (coupling of a
carbonyl compound and an isocyanide with a carboxylic acid
to form an R-acyloxycarboxamide) increases structural com-
plexity; however, methods to control the stereochemical
outcome of the carbon-carbon bond when simple achiral


Source: Andreana, Peter R. - Department of Chemistry, Wayne State University


Collections: Chemistry