1531624-29-9Relevant academic research and scientific papers
Asymmetric Nucleophilic Catalysis with an Octahedral Chiral-at-Metal Iridium(III) Complex
Cruchter, Thomas,Medvedev, Michael G.,Shen, Xiaodong,Mietke, Thomas,Harms, Klaus,Marsch, Michael,Meggers, Eric
, p. 5151 - 5162 (2017/08/17)
Herein, we report about the design, synthesis, and application of a nucleophilic octahedral chiral-only-at-metal iridium(III) complex. We demonstrate that the enantiopure form of this complex serves as an efficient catalyst for the asymmetric Steglich rearrangement of O-acylated azlactones (up to 96% ee and 99% yield) and the related asymmetric Black rearrangement of O-acylated benzofuranones (up to 94% ee and 99% yield). We provide insight into the mechanisms of these two acyl migration reactions and the catalyst's manner of chiral recognition with crystal structures of the active catalyst and a catalysis intermediate analog, as well as with quantum chemical calculations based on them. Furthermore, we demonstrate that the presented catalyst also efficiently catalyzes the asymmetric reaction between aryl alkyl ketenes and 2-cyanopyrrole to give the corresponding α-chiral N-acyl pyrroles (up to 95% ee and 99% yield).
Enantioselective Black rearrangement catalyzed by chiral bicyclic imidazole
Wang, Mingli,Zhang, Zhenfeng,Liu, Shan,Xie, Fang,Zhang, Wanbin
, p. 1227 - 1230 (2014/02/14)
A newly developed chiral imidazole nucleophilic catalyst, Acyloxy-DPI, was readily prepared and successfully applied to the enantioselective Black rearrangement with up to 88% ee for a wide range of substrates possessing different substituted groups. A pl
