447461-88-3Relevant academic research and scientific papers
Enantioselective 1,4-addition of aromatic nucleophiles to alpha,beta-unsaturated aldehydes using chiral organic catalysts
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Page 11, (2010/02/03)
Nonmetallic, chiral organic catalysts are used to catalyze the 1,4-addition of an aromatic nucleophile to an α,β-unsaturated aldehyde. The aromatic nucleophile may be an N,N-disubstituted aniline compound, or an analog thereof. The reaction is efficient a
The enantioselective organocatalytic 1,4-addition of electron-rich benzenes to α,β-unsaturated aldehydes
Paras, Nick A.,MacMillan, David W. C.
, p. 7894 - 7895 (2007/10/03)
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. Copyright
