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Rate Acceleration of Triethylamine‐Mediated Guanidine‐ Catalyzed Enantioselective Michael Reaction
Author(s) -
Jiang Zhiyong,
Ye Weiping,
Yang Yuanyong,
Tan ChoonHong
Publication year - 2008
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.200800423
Subject(s) - triethylamine , michael reaction , chemistry , enantioselective synthesis , guanidine , adduct , enantiomer , catalysis , bicyclic molecule , organic chemistry , solvent , medicinal chemistry , enantiomeric excess
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 (Et 3 N) 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%).