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Williams, Garrett; Lecakes, George; Almon, Amanda; Koutsoubis, Nikolas; Naddeo, Kyle; Kiel, Thom; Ditzler, Gregory; Bouaynaya, Nidhal (, Proceedings Volume 12529, Synthetic Data for Artificial Intelligence and Machine Learning: Tools, Techniques, and Applications)Manser, Kimberly E.; Rao, Raghuveer M.; Howell, Christopher L. (Ed.)
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Bergstrom, Benjamin D.; Toth-Williams, Garrett; Lo, Anna; Toman, Jeffrey W.; Fettinger, James. C.; Shaw, Jared T. (, The Journal of Organic Chemistry)
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Lo, Anna; Gutierrez, David A.; Toth-Williams, Garrett; Fettinger, James C.; Shaw, Jared T. (, The Journal of Organic Chemistry)
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Gutierrez, David_A; Toth‐Williams, Garrett; Laconsay, Croix_J; Yasuda, Michael; Fettinger, James_C; Di_Maso, Michael_J; Shaw, Jared_T (, Angewandte Chemie International Edition)Abstract Herein we report the first transition metal‐catalyzed approach to the enantioenriched synthesis of cyclic sulfonimidamides relying on commercially available palladium catalysts and ligands. High‐throughput experimentation (HTE) was employed to identify the optimal catalyst system and solvent. The method is applied to a variety of saturated and unsaturated rings and exhibits the highest selectivity for 2‐substituted allyl electrophiles. The products are further elaborated to complex, tricyclic scaffolds. DFT experiments presented herein highlight the key ligand substrate interactions leading to the high levels of enantioselectivity.more » « less
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