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Issue 6, 2011

Catalytic, enantioselective synthesis of stilbenecis-diamines: A concise preparation of (−)-Nutlin-3, a potent p53/MDM2 inhibitor

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Abstract

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-stilbene diamines 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.

Graphical abstract: Catalytic, enantioselective synthesis of stilbenecis-diamines: A concise preparation of (−)-Nutlin-3, a potent p53/MDM2 inhibitor

Supplementary files

Article information


Submitted
28 Jan 2011
Accepted
24 Feb 2011
First published
25 Mar 2011

Chem. Sci., 2011,2, 1076-1079
Article type
Edge Article

Catalytic, enantioselective synthesis of stilbenecis-diamines: A concise preparation of (−)-Nutlin-3, a potent p53/MDM2 inhibitor

T. A. Davis and J. N. Johnston, Chem. Sci., 2011, 2, 1076 DOI: 10.1039/C1SC00061F

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