1318802-50-4Relevant academic research and scientific papers
Chiral DMAP-N-oxides as Acyl Transfer Catalysts: Design, Synthesis, and Application in Asymmetric Steglich Rearrangement
Xie, Ming-Sheng,Zhang, Ye-Fei,Shan, Meng,Wu, Xiao-Xia,Qu, Gui-Rong,Guo, Hai-Ming
supporting information, p. 2839 - 2843 (2019/02/16)
A DMAP-N-oxide, featuring an α-amino acid as the chiral source, was developed, synthesized and applied in asymmetric Steglich rearrangement. A series of O-acylated azlactones afforded C-acylated azlactones possessing a quaternary stereocenter in high yiel
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).
The pyridine derivative or a salt thereof having axial asymmetry, and the manufacture thereof as well as asymmetric catalyst comprising
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Paragraph 0143; 0144, (2017/08/02)
Provided is a pyridine derivative represented by general formula (1) or a salt thereof, by which an optically active form can be obtained with favorable enantioselectivity. (In the formula, R1 to R6 and R1' to R6' each independently are a hydrogen atom, a
Catalytic enantioselective Steglich rearrangements using chiral N-heterocyclic carbenes
Campbell, Craig D.,Concellon, Carmen,Smith, Andrew D.
experimental part, p. 797 - 811 (2011/08/06)
The evaluation of a range of enantiomerically pure NHCs, prepared in situ from imidazolinium or triazolium salt precatalysts, to promote the catalytic enantioselective Steglich rearrangement of oxazolyl carbonates to their C-carboxyazlactones, is reported. Modest levels of enantioselectivity (up to 66% ee) are observed using oxazolidinone derived NHCs.
