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Gelatin Protein‐Mediated Direct Aldol Reaction
Author(s) -
Kühbeck Dennis,
Bachl Jürgen,
Schön EvaMaria,
GotorFernández Vicente,
Díaz Díaz David
Publication year - 2014
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.201300380
Subject(s) - cyclohexanone , aldol reaction , chemistry , yield (engineering) , gelatin , reaction rate constant , reaction rate , organic chemistry , kinetics , catalysis , materials science , physics , quantum mechanics , metallurgy
Gelatin protein was found to catalyze the aldol reaction between cyclohexanone and different aromatic aldehydes under mild reaction conditions. The aldol additions carried out in DMSO at 37° yielded the addition products with moderate diastereoselectivities favoring the syn isomers. Appropriate control experiments demonstrated the activity of the protein in the aldol reaction. The kinetic study of the model reaction between 4‐nitrobenzaldehyde and cyclohexanone established a first‐order rate constant k =(7.4±0.5)×10 −3 h −1 . Moreover, the scale‐up of the process was successfully achieved at 1‐g scale in a yield comparable to that in small scale.