76154-00-2Relevant articles and documents
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.
Nickel-Catalyzed Benzylic Substitution of Benzyl Esters with Malonates as a Soft Carbon Nucleophile
Tsuji, Hiroaki,Hashimoto, Keisuke,Kawatsura, Motoi
, p. 8837 - 8841 (2019/11/11)
The nickel-catalyzed benzylic substitution of benzyl alcohol derivatives with a soft carbon nucleophile is extremely rare compared to that with a hard carbon nucleophile. We have achieved the nickel-catalyzed benzylic substitution of benzyl esters with malonates as a soft carbon nucleophile. Primary and secondary benzyl 2,3,4,5,6-pentafluorobenzoates as well as a wide variety of malonate derivatives were well tolerated in the nickel-catalyzed reaction, providing the corresponding alkylation products in 46-86% yields (34 examples). Additionally, we propose a possible reaction mechanism that would undergo via the ??1- A nd ??3-benzylnickel intermediates.
Pyran-2-ones and 5,6-dihydropyran-2-ones useful for treating hyperplasia and other diseases
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, (2010/02/05)
Certain 2H-pyran-2-ones are useful for treating benign prostatic hypertrophy or hyperplasia, prostatic cancer, alopecia, hirsutism, acne vulgaris and seborrhea.
Synthesis of substituted cyclopropanes from 1,3-diols through the corresponding cyclic sulfates
Guijarro, David,Yus, Miguel
, p. 11445 - 11456 (2007/10/02)
The reaction of different cyclic sulfates 2 (easily prepared from the corresponding 1,3-diols 1 following the Sharpless methodology) with an excess of lithium powder and a catalytic amount of DTBB (5 mol %) leads to the corresponding substituted cyclopropanes 3 through a γ-elimination process, the sulfate ion acting as leaving group.
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.
Alkylation of Monosubstituted Malonate Anions With Pyridinium and Quinolinium Salts
Katritzky, Alan R.,Aurrecoechea, Jose M.
, p. 342 - 345 (2007/10/02)
Monosubstituted malonate anions are alkylated at room temperature with 1-(sec-alkyl)quinolinium salts.Hindered disubstituted malonate esters can thus be prepared under very mild conditions.
THE SRN2 MECHANISM OF NUCLEOPHILIC SUBSTITUTION
Katritzky, Alan R.,Ville, George Z. de,Patel, Ranjan C.
, p. 1723 - 1726 (2007/10/02)
1-Alkylpyridiniums react with nitroalkane and ethylmalonate anions by a radical nucleophilic substitution mechanism not involving radical chains.
