%0 Journal Article
%A Paras, Nick A.
%A W. C. MacMillan, David
%D 2002
%T The Enantioselective Organocatalytic 1,4-Addition of Electron-Rich Benzenes
to α,β-Unsaturated Aldehydes
%U https://acs.figshare.com/articles/journal_contribution/The_Enantioselective_Organocatalytic_1_4-Addition_of_Electron-Rich_Benzenes_to_-Unsaturated_Aldehydes/3642954
%R 10.1021/ja025981p.s001
%2 https://acs.figshare.com/ndownloader/files/5731758
%K enantioselective organocatalytic alkylation
%K benzylic stereogenicity
%K chiral synthon
%K aldehyde substrates
%K butylimidazolidinone amine catalyst
%K iminium catalysis
%K catalyst quantities
%K mol
%K conjugate addition
%K agent synthesis
%K catalyst loadings
%K unsubstituted anilines
%K organocatalytic transformation
%K enantioselective construction
%X The first enantioselective organocatalytic alkylation of electron-rich benzene rings with α,β-unsaturated aldehydes has been accomplished. The use of iminium catalysis has provided a new strategy for the enantioselective construction of benzylic stereogenicity, an important chiral synthon for natural product and medicinal agent synthesis. The (2S,5S)-5-benzyl-2-tert-butylimidazolidinone amine catalyst has been found to mediate the conjugate addition of a wide variety of substituted and unsubstituted anilines to unsaturated aldehydes. A diverse spectrum of aldehyde substrates can also be accommodated in this new organocatalytic transformation. While catalyst quantities of 10 mol % were generally employed in this study, successful alkylations conducted with catalyst loadings as low as 1 mol % are described.
%I ACS Publications