58635-83-9Relevant 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
, (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.
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.
Styrene-acrylic acid synthetic method of the compound
-
Paragraph 0030; 0046; 0051; 0052, (2017/05/02)
The invention discloses a method for directly achieving direct arylation reaction of benzene and carbonyl beta-bite sp3C-H bonds employing palladium acetate as a catalyst under the action of bidentate guide base, so as to synthesize a phenylpropionic acid compound. The method comprises the following steps: sequentially adding a 2-propionamido-pyridine-1-oxide, palladium acetate, gibbsite dipotassium phosphate, an aryl iodide compound and dimethylsulfoxide to a shrek tube in an air atmosphere, and reacting for 20-30 hours; after the reaction is ended, cooling to a room temperature, extracting, drying, concentrating and carrying out chromatographic separation to obtain an arylated product; dissolving the obtained arylated product into an ethanol solution of NaOH and reacting for 20-30 hours; and after reaction is ended, neutralizing, extracting, drying, concentrating and carrying out column chromatography to obtain the phenylpropionic acid compound. The method is mild in reaction condition, and good in functional group tolerance; an external additive is not needed; and the carbonyl beta-bite sp3C-H bonds in the 2-propionyl aminopyridine-1-oxide can be directly arylated.
A method to prepare optically active acyclic α-benzyl ketones by thermodynamically controlled deracemization
Kaku, Hiroto,Imai, Takahiro,Kondo, Risa,Mamba, Shiho,Watanabe, Yu,Inai, Makoto,Nishii, Takeshi,Horikawa, Mitsuyo,Tsunoda, Tetsuto
supporting information, p. 8208 - 8213 (2014/01/06)
Thermodynamically controlled deracemization of some acyclic ketones bearing a chiral center at the position α to the carbonyl group was satisfactorily achieved. Acyclic ketones with high optical purities could be isolated after treatment of the racemic ketones with base in aqueous MeOH in the presence of (-)-(2R,3R)-trans-2,3-bis(hydroxydiphenylmethyl)-1,4-dioxaspiro[5. 4]decane (1a). The efficiency of the deracemization was appreciably influenced by the ratio of H2O/MeOH used as solvent. Racemic ketones bearing a chiral center at the position α to the carbonyl group were converted into optically active ketones in the presence of TADDOL-type host molecule 1a in H2O/MeOH in suspension in basic media. Copyright
Influence of the position of the substituent on the efficiency of lipase-mediated resolutions of 3-aryl alkanoic acids
Deasy, Rebecca E.,Moody, Thomas S.,Maguire, Anita R.
, p. 1480 - 1487 (2013/12/04)
Hydrolase-catalysed kinetic resolutions to provide enantioenriched α-substituted 3-aryl alkanoic acids are described. (S)-2-Methyl-3- phenylpropanoic acid (S)-1a was prepared in 96% ee by Pseudomonas fluorescens catalysed ester hydrolysis, while, Candida antarctica lipase B (immob) resolved the α-ethyl substituted 3-arylalkanoic acid (R)-1b in 82% ee. The influence of the position of the substituent relative to the ester site on the efficiency and enantioselectivity of the biotransformation is also explored; the same lipases were found to resolve both the α- and β-substituted alkanoic acids. Furthermore, the steric effect of substituents at the C2 stereogenic centre relative to that for their C3 substituted counterparts on the efficiency and stereoselectivity is discussed.
Structural requirements for substrate in highly enantioselective hydrogenation over the cinchonidine-modified Pd/C
Sugimura, Takashi,Uchida, Takayuki,Watanabe, Junya,Kubota, Takeshi,Okamoto, Yasuaki,Misaki, Tomonori,Okuyama, Tadashi
experimental part, p. 57 - 64 (2009/06/17)
Relationship between substrate structure and enantioselectivity is studied for the asymmetric hydrogenation of 42 different (E)-α, β-disubstituted acrylic acids (propenoic acids) over cinchonidine-modified Pd/C. The β-phenyl group is indispensable for high enantioselectivity of α-phenylcinnamic acid (2,3-diphenylpropenoic acid, 81% ee), and substitution on this group affects markedly the selectivity. The high ee up to 92% was achieved by the β - p-alkoxyphenyl substitution, and the selectivity is ascribed mainly to stronger interaction of the substrate with the chiral modifier on the catalyst surface. In contrast, substitution on the α-phenyl group does not affect notably the enantioselectivity (80-82% ee) or even the α-phenyl group itself is not indispensable but replaceable with a properly bulky group for the high enantioselectivity.
Organocatalytic Michael addition of aldehydes to vinyl sulfones: Enantioselective α-alkylations of aldehydes and their derivatives
Zhu, Qiang,Lu, Yixin
supporting information; experimental part, p. 4803 - 4806 (2009/05/31)
(Equation Presented) Organocatalytic asymmetric Michael reaction of unmodified aldehydes to vinyl sulfones catalyzed by silylated biarylprolinol afforded the desired Michael products with exceptional enantioselectivity. The described enantioselective addition to vinyl sulfones, in combination with desulfonation, offers a unique, asymmetric entry to α-alkylated aldehydes and their derivatives.
Remarkable electronic and steric effects in the nitrile biotransformations for the preparation of enantiopure functionalized carboxylic acids and amides: Implication for an unsaturated carbon-carbon bond binding domain of the amidase
Gao, Ming,Wang, De-Xian,Zheng, Qi-Yu,Huang, Zhi-Tang,Wang, Mei-Xiang
, p. 6060 - 6066 (2008/02/10)
(Chemical Equation Presented) Biotransformations of various functionalized racemic nitriles catalyzed by Rhodococcus erythropolis AJ270, a nitrile hydratase/amidase-containing microbial whole-cell catalyst, were studied. While the nitrile hydratase exhibi
Asymmetric synthesis of novel α-amino acids with β-branched side chains
Zhang, Minsheng,Porte, Alex,Diamantidis, George,Sogi, Kimberly,Kubrak, Dennis,Resnick, Lynn,Mayer, Scott C.,Wang, Zheng,Kreft, Anthony F.,Harrison, Boyd L.
, p. 2401 - 2403 (2008/02/03)
An asymmetric synthesis of α-amino acids with novel β-branched side chains has been implemented. The syntheses feature a p-toluenesulfinylimine induced chiral Strecker approach and were found to be applicable to the introduction of both aliphatic and aromatic β-branched sidechains for preparation of previously unknown α-amino acids.
Design and synthesis of a new polymer-supported Evans-type oxazolidinone: An efficient chiral auxiliary in the solid-ph ase asymmetric alkylation reactions
Kotake, Tomoya,Hayashi, Yoshio,Rajesh,Mukai, Yoshie,Takiguchi, Yuka,Kimura, Tooru,Kiso, Yoshiaki
, p. 3819 - 3833 (2007/10/03)
Wang resin-supported Evans' chiral auxiliary (23) was designed based on a novel polymer-anchoring strategy, which utilizes the 5-position of the oxazolidinone ring, and its new synthetic route applicable to multi-gram preparation in just a day was developed. Solid-phase Evans' asymmetric alkylation on 23-derived N-acylimide resin and following lithium hydroperoxide-mediated chemoselective hydrolysis afforded the corresponding α-branched carboxylic acids in desired high stereoselectivities (up to 97% ee) and moderate to good overall yield (up to 70%, for 3 steps), which were comparable to those of the conventional solution-phase methods. Furthermore, recovery and recycling of the polymer-supported chiral auxiliary were successfully achieved without decreasing the stereoselectivity of the product. Therefore, this is the first successful example that the solid-phase Evans' asymmetric enolate-alkylation was efficiently performed on the solid-support, and it is concluded that the connection to the solid-support via the 5-position of the oxazolidinone ring is an ideal strategy in the solid-phase Evans' chiral auxiliary.
