57918-88-4Relevant academic research and scientific papers
Carbonylative Transformation of Allylarenes with CO Surrogates: Tunable Synthesis of 4-Arylbutanoic Acids, 2-Arylbutanoic Acids, and 4-Arylbutanals
Wu, Fu-Peng,Li, Da,Peng, Jin-Bao,Wu, Xiao-Feng
supporting information, p. 5699 - 5703 (2019/08/01)
In this Communication, procedures for the selective synthesis of 4-arylbutanoic acids, 2-arylbutanoic acids, and 4-arylbutanals from the same allylbenzenes have been developed. With formic acid or TFBen as the CO surrogate, reactions proceed selectively and effectively under carbon monoxide gas-free conditions.
A Study of Enantioselective Reduction of para-Substituted 2-Methyl-cinnamaldehydes by Baker's Yeast
Sunjic, Vitomir,Majeric, Maja,Hamersak, Zdenko
, p. 643 - 660 (2007/10/03)
Reduction of a series of para-substituted 2-methyl-cinnamaldehydes (1-7) at 20°C and at pH = 2-3 afforded S-enantiomers of saturated alcohols 8-14 in 20-80% yield and 75 - ≥ 99% enantiomeric excess (e.e.); at 30°C, lower yields and e.e.s were obtained. Relative rates of the formation of allylic alcohols 15-21, catalyzed by alcohol dehydrogenase (ADH), correlate with the Hammett σ+ values of para-substituents, revealing that a more efficient delocalization of the positive charge on carbonylic carbon slow down the reduction rates, whereas no correlation of the electronic properties of the substituents with the rate of C=C double bond reduction, catalyzed by enoate reductase, is observed. On reduction of 3 by dried yeast in 2H2O, α,β-carbon atoms in 10a bear 2H atoms, in accordance with the previously reported hydrogenation of selectively 2H-labeled cinnamic aldehyde and cinnamic alcohol. The accumulated data indicate that the mechanism of the enone C=C bond reduction that comprises nucleophilic attack of the hydride ion species on the β-carbon in the first step, followed by enantioselective protonation on the α-carbon atom.
