1379367-09-5Relevant academic research and scientific papers
Borylation of Unactivated C(sp3)-H Bonds with Bromide as a Traceless Directing Group
Zhang, Ge,Li, Meng-Yao,Ye, Wen-Bo,He, Zhi-Tao,Feng, Chen-Guo,Lin, Guo-Qiang
, p. 2948 - 2953 (2021/05/05)
A palladium-catalyzed alkyl C-H borylation with bromide as a traceless directing group is described, providing a convenient approach to access alkyl boronates bearing a β-all-carbon quaternary stereocenter. The protocol features a broad substrate scope, excellent site selectivity, and good functional group tolerance.
Concise Synthesis of 2-Arylpropanoic Acids and Study of Unprecedented Reduction of 3-Hydroxy-2-arylpropenoic Acid Ethyl Ester to 2-Arylpropenoic Acid Ethyl Ester by BH3·THF
Shahid Islam,Ahmad, Syarhabil,Attu, Mary Rose,Foerstering, F. Holger,Mahmun Hossain
, p. 1273 - 1286 (2015/09/22)
We have developed a concise method of synthesizing racemic arylpropanoic acids, which have been widely used as nonsteroidal anti-inflammatory drugs (NSAIDs). The synthesis involves only four steps from commercially available benzaldehyde. The synthesis incorporates an unprecedented reduction reaction, conversion of 3-hydroxy-2-arylpropenoic acid ethyl ester to 2-arylpropenoic acid ethyl ester by BH3·THF. The reduction reaction has been investigated and optimized.
A new method for production of chiral 2-aryl-2-fluoropropanoic acids using an effective kinetic resolution of racemic 2-aryl-2-fluoropropanoic acids
Tengeiji, Atsushi,Shiina, Isamu
experimental part, p. 7356 - 7378 (2012/09/05)
We report a new method for the preparation of chiral 2-aryl-2- fluoropropanoic acids, including 2-fluoroibuprofen, a fluorinated analogue of non-steroidal anti-inflammatory drugs (NSAIDs), by the kinetic resolution of racemic 2-aryl-2-fluoropropanoic acids using enantioselective esterification. By applying pivalic anhydride (Piv2O) as a coupling agent, bis(α-naphthyl)methanol [(α-Np)2CHOH] as an achiral alcohol, and (+)-benzotetramisole (BTM) as a chiral acyl-transfer catalyst, a series of racemic 2-aryl-2-fluoropropanoic acids were kinetically separated to afford the optically active carboxylic acids and the corresponding esters with good to high enantiomeric excesses. This technology can provide a convenient approach to furnish the chiral a-fluorinated drugs containing quaternary carbons at the α-positions in the 2-aryl-2-fluoropropanoic acid structure.
