Chemoselective,accelerated and stereoselective aza-Michael addition of amines to N-phenylmaleimide by using TMEDA based receptors |
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Institution: | 1. College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310014, China;2. Key Laboratory of Drug Prevention and Control Technology of Zhejiang Province, Zhejiang Police College, Hangzhou, 310053, China;3. Key Laboratory of Drug Monitoring and Control of Zhejiang Province, National Anti-Drug Laboratory Zhejiang Regional Center, Hangzhou, 310053, China |
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Abstract: | An aza-Michael addition between a maleimide and amines is described in which the presence of simple amine receptors (TMEDA or trans-TMCDA) promote the chemoselectivity of the reaction (respectively, 1,2- and 1,4-addition). Additionally, both receptors are able to accelerate the reaction. Stoichiometries of complexes between receptors and amines were determined by 1H NMR dilution experiments while enantiomeric excesses were observed on 1,4-adducts by using (1R,2R)-TMCDA. |
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