Parameterization of Acyclic Diaminocarbene Ligands Applied to a Gold(I)-Catalyzed Enantioselective Tandem Rearrangement/Cyclization.
- Author(s): Niemeyer, Zachary L;
- Pindi, Suresh;
- Khrakovsky, Dimitri A;
- Kuzniewski, Christian N;
- Hong, Cynthia M;
- Joyce, Leo A;
- Sigman, Matthew S;
- Toste, F Dean
- et al.
Published Web Locationhttps://doi.org/10.1021/jacs.7b08791
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.