Chemistry and Chemical Bioengineering Unit, Okinawa Institute of Science and Technology Graduate University, 1919-1 Tancha, Onna, Okinawa 904-0495, Japan.
Faculty of Advanced Life Science, Hokkaido University, Kita 21 Nishi 11, Sapporo 001-0021, Japan.
Org Lett. 2022 Mar 11;24(9):1853-1858. doi: 10.1021/acs.orglett.2c00436. Epub 2022 Feb 28.
Enantioselective Mannich reactions of pyruvates catalyzed by amine-based catalyst systems, in which pyruvates act as nucleophiles, are reported. The reactions of pyruvates and cyclic sulfonylimines afforded the desired Mannich products, including those bearing tetrasubstituted carbon centers, in high yields with high enantioselectivities in most cases. The selection of the acid used in the amine-based catalyst system was key for the formation of the Mannich products with high enantioselectivities.
手性胺催化丙酮酸的对映选择性 Mannich 反应,其中丙酮酸作为亲核试剂,被报道。丙酮酸和环状亚磺酰亚胺的反应以高收率和高对映选择性(在大多数情况下)得到所需的 Mannich 产物,包括那些带有四取代碳原子中心的产物。在基于胺的催化剂体系中使用的酸的选择对于形成具有高对映选择性的 Mannich 产物是关键的。