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The first highly diastereo- and enantioselective additions of aryl nitromethane pronucleophiles to aryl aldimines are described. Identification of an electron rich chiral Bis(AMidine)catalyst for this aza-Henry variant was key to this development, leading ultimately to differentially protected cis-stilbenediamines in two steps. This method then became the lynchpin for an enantioselective synthesis of (−)-Nutlin-3 (Hoffmann-La Roche), a potent cis-imidazoline small molecule inhibitor of p53-MDM2 used extensively as a probe of cell biology and currently in drug development.
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