3453-64-3Relevant articles and documents
Pt-Catalyzed sp3 C-H bond activation of o-alkyl substituted aromatic carboxylic acid derivatives for the formation of aryl lactones
Lee, Ji Min,Chang, Sukbok
, p. 1375 - 1379 (2006)
Synthesis of aryl lactones from ortho-alkyl substituted aromatic carboxylic acids is described on the basis of sp3 C-H bond activation using either palladium or platinum catalysts. Kinetic isotope studies reveal that the reaction takes place presumably by the chelation assistance of metal catalyst to the carboxylic group followed by the C-H bond activation.
Ruthenium-Catalyzed Enantioselective Hydrogenation/Lactonization of 2-Acylarylcarboxylates: Direct Access to Chiral 3-Substituted Phthalides
Lu, Bin,Zhao, Mengmeng,Ding, Guangni,Xie, Xiaomin,Jiang, Lili,Ratovelomanana-Vidal, Virginie,Zhang, Zhaoguo
, p. 3989 - 3996 (2017/09/13)
Highly enantioselective tandem hydrogenation/lactonization of various 2-acylarylcarboxylates including 2-aroylarylcarboxylates were realized by using [RuCl(benzene)(S)-SunPhos]Cl as the catalyst under mild reaction conditions. Excellent enantioselectivities (up to 99.6 % ee) and activities (S/C=1000) were obtained. This convenient and practical method enables a direct access to a series of highly optically pure 3-substituted phthalides that are very important molecules as valuable pharmacological compounds and diversified synthons for medicinal chemistry. Moreover, a gram-scale reaction was performed to further demonstrate the practicality of this approach.
P450 BM3-Catalyzed Regio- and Stereoselective Hydroxylation Aiming at the Synthesis of Phthalides and Isocoumarins
Holec, Claudia,Hartrampf, Ute,Neufeld, Katharina,Pietruszka, J?rg
, p. 676 - 684 (2017/04/11)
Cytochrome P450 BM3 monooxygenases are able to catalyze the regio- and stereoselective oxygenation of a broad range of substrates, with promising potential for synthetic applications. To study the suitability of P450 BM3 variants for stereoselective benzylic hydroxylation of 2-alkylated benzoic acid esters, the biotransformation of methyl 2-ethylbenzoate, resulting in both enantiomeric forms of 3-methylphthalide, was investigated. In the case of methyl 2-propylbenzoate as a substrate the regioselectivity of the reaction was shifted towards β-hydroxylation, resulting in the synthesis of enantioenriched R- and S-configured 3-methylisochroman-1-one. The potential of P450 BM3 variants for regio- and stereoselective synthesis of phthalides and isocoumarins offers a new route to a class of compounds that are valuable synthons for a variety of natural compounds.
Phthalides by rhodium-catalyzed ketone hydroacylation
Phan, Diem H. T.,Kim, Byoungmoo,Dong, Vy M.
supporting information; experimental part, p. 15608 - 15609 (2010/01/30)
(Chemical Equation Presented) Phthalides are biologically relevant five-membered lactones found in herbs, fruits, and vegetables. Herein we communicate the first atom-economical approach to phthalides by using enantioselective ketone hydroacylation. In the presence of Rh[(Duanphos)]X (X = NO3, OTf, OMs), various 2-ketobenzaldehydes undergo intramolecular hydroacylation to produce phthalide products in good yields and 92-98% ee's. Our study highlights the key role counterions play in controlling both reactivity and enantioselectivity. A concise asymmetric total synthesis of the celery extract (S)-(-)-3-n-butylphthalide is also presented.
Novel Reduction of Carboxylic Acids, Esters, Amides and Nitriles Using Samarium Diiodide in the Presence of Water
Kamochi, Yasuko,Kudo, Tadahiro
, p. 1495 - 1498 (2007/10/02)
Aromatic carboxylic acids, esters, amides, nitriles, chlorides, ketones and nitro compounds were rapidly reduced by the samarium diiodide-H2O system to the corresponding products at room temperature in good yields.
