Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 76, Issue 5, Pages 1464-1467Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo1022469
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- Conacyt, Mexico [60366, 22211]
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The organocatalytic activity of the methyl ester of (S)-proline-(S)-phenylalanine, (S,S)-2, in the asymmetric aldol reaction between cyclohexanone and acetone with various aromatic aldehydes under solvent-free conditions in a ball mill has been evaluated. alpha,alpha-Dipeptide (S,S)-2 catalyzed the stereoselective formation of the expected aldol products, with higher diastereo- and enantioselectivity relative to similar reactions in solution, up to 91:9 anti:syn diastereomeric ratio and up to 95% enantiomeric excess.
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