Journal
TETRAHEDRON
Volume 72, Issue 21, Pages 2690-2699Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2015.09.068
Keywords
Cycloaddition; Asymmetric catalysis; Sliver; Azomethine ylide; Phosphine; Atropisomer
Categories
Funding
- National Natural Science Founder of China [21173064, 21133011, 21472031]
- Zhejiang Provincial Natural Science Foundation of China [LR14B030001]
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Simple modifications of our novel ligand (Xing-Phos) were presented in this work, and a series of aromatic tertiary amide derived non-biaryl atropisomers were successfully synthesized in good yields. In addition, it was found that the multifunctional aromatic tertiary amide derived non-biaryl atropisomers exhibited an excellent endo-selectivity in the silver-catalyzed [3+2]-cycloaddition of azomethine ylides with N-aromatic maleimide. And especially, good to high levels of enantioselectivity (up to 98% ee) was obtained with a wide range of substrates in the presence of syn-(R, R-S)-2a (Xing-Phos). Furthermore, on the basis of the experimental data, it was demonstrated that a trace amount of water play an important role in the enhancement of enantioselectivity. (C) 2015 Elsevier Ltd. All rights reserved.
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