4379-25-3Relevant academic research and scientific papers
Synthesis and olfactory evaluation of optically active β-alkyl substituted γ-lactones and whiskey lactone analogues
Kato, Daiki,Kawasaki, Masashi,Morita, Yuko,Okada, Takuya,Tanaka, Yasuo,Toyooka, Naoki
supporting information, (2020/02/22)
Optically active β-alkyl substituted γ-lactones and whiskey lactone analogues were synthesized, and the odor properties were evaluated. During the preparation of the chiral intermediates, we found good reaction conditions for the highly enantioselective esterification of 3-arylmethyl-2-methyl-1-propanols to kinetically resolve them. The results of the olfactory evaluations of the synthesized lactones revealed that the alkyl groups on the γ-lactone rings played an important role for the odor profiles.
CHEMOENZYMATIC SYNTHESIS OF THE ENANTIOMERS OF IOPANOIC ACID
Colombo, M.,Amici, M. De,Micheli, C. De,Pitre, D.,Carrea, G.,Riva, S.
, p. 1021 - 1030 (2007/10/02)
The two enantiomers of Iopanoic acid 1 were prepared in enantiomeric excess higher than 90percent by enzyme-catalyzed hydrolysis of precursors (+/-)-2a and (+/-)-3a, followed by standard chemical transformations.Among the tested enzymes, chymotrypsin and Lipase PS proved to be the most selective catalysts.The stereochemical outcome of the lipase-catalyzed hydrolyses of esters (+/-)-2a-d is strictly dependent upon both the size of the alkyl group attached to the chiral center and the substituent in the aromatic ring.The enantioselectivity of the reactions was evaluated by chiral HPLC and the configurations of the new products were assigned by chemical correlations.
