Journal of the American Chemical Society
Journal of the American Chemical Society
5 years ago

Parameterization of Acyclic Diaminocarbene Ligands Applied to a Gold(I)-Catalyzed Enantioselective Tandem Rearrangement/Cyclization

Parameterization of Acyclic Diaminocarbene Ligands Applied to a Gold(I)-Catalyzed Enantioselective Tandem Rearrangement/Cyclization
F. Dean Toste, Leo A. Joyce, Christian N. Kuzniewski, Zachary L. Niemeyer, Matthew S. Sigman, Dimitri A. Khrakovsky, Cynthia M. Hong, Suresh Pindi
Computed descriptors for acyclic diaminocarbene ligands are developed in the context of a gold catalyzed enantioselective tandem [3,3]-sigmatropic rearrangement-[2+2]-cyclization. Surrogate structures enable the rapid identification of parameters that reveal mechanistic characteristics. The observed selectivity trends are validated in a robust multivariate analysis facilitating the development of a highly enantioselective process.

Publisher URL: http://dx.doi.org/10.1021/jacs.7b08791

DOI: 10.1021/jacs.7b08791

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