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Title: Rate acceleration of triethylamine-mediated guanidine-catalyzed enantioselective Michael reaction
Authors: Jiang, Z. 
Ye, W.
Yang, Y.
Tan, C.-H. 
Keywords: Asymmetric catalysis
Chiral bicyclic guanidines
Michael addition
Organic catalysis
Triethylamine (Et3N)
Issue Date: 6-Oct-2008
Citation: Jiang, Z., Ye, W., Yang, Y., Tan, C.-H. (2008-10-06). Rate acceleration of triethylamine-mediated guanidine-catalyzed enantioselective Michael reaction. Advanced Synthesis and Catalysis 350 (14-15) : 2345-2351. ScholarBank@NUS Repository.
Abstract: A chiral bicyclic guanidine was found to be an excellent catalyst for enantioselective Michael reactions. It was observed that additives such as non-chiral amines could accelerate the rate of reaction. When triethylamine (Et3N) was as used as the solvent, the reaction rate can be increased up to 1000 times without compromising the enantioselectivity. Michael acceptors such as 2-cyclopenten-1-one 2 and N-alkylmaleimides were investigated, with various commercially available Michael donors such as dialkyl malonates and benzoylactetates. Michael adducts were obtained in excellent enantiomeric excesses (up to 96%) and yields (up to 99%). © 2008 Wiley-VCH Verlag GmbH & Co. KGaA.
Source Title: Advanced Synthesis and Catalysis
ISSN: 16154150
DOI: 10.1002/adsc.200800423
Appears in Collections:Staff Publications

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