17257-71-5Relevant articles and documents
Probing the parallel resolution of Mosher's acid using a combination of quasi-enantiomeric oxazolidin-2-ones
Chavda, Sameer,Coulbeck, Elliot,Dingjan, Marco,Eames, Jason,Motevalli, Majid
, p. 1274 - 1284 (2008/12/20)
Mosher's acid (2-methoxy-2-phenyl-2-trifluoromethylacetic acid) was resolved by parallel resolution of its corresponding pentafluorophenyl active ester using a quasi-enantiomeric combination of oxazolidin-2-ones.
Enantioselective synthesis of arylmethoxyacetic acid derivatives
Moreno-Dorado, F. Javier,Guerra, Francisco M.,Ortega, Maria J.,Zubia, Eva,Massanet, Guillermo M.
, p. 503 - 510 (2007/10/03)
The preparation of several arylmethoxyacetic acids by a sequence of asymmetric dihydroxylation and further oxidation of the resulting glycol with TEMPO/NaClO/NaClO2 is described. The scope and limitations of the reaction are discussed.
Chiral discrimination of 2-arylalkanoic acids by (1S,2R)-1-aminoindan-2-ol through the formation of a consistent columnar supramolecular hydrogen-bond network
Kinbara, Kazushi,Kobayashi, Yuka,Saigo, Kazuhiko
, p. 111 - 119 (2007/10/03)
Enantiopure cis-1-aminoindan-2-ol was selected as a basic resolving agent for racemic 2-arylalkanoic acids on the basis that its rigid cis-conformation would favor the formation of a supramolecular hydrogen-bonded column, in which chiral discrimination of the racemic carboxylate would occur. It was found that this amino alcohol possesses high resolving efficiency for a variety of racemic acids; also, X-ray crystallographic analyses of the diastereomeric salts showed that a columnar hydrogen-bond network is formed in both the less- and more-soluble diastereomeric salts, as we had expected. A detailed study on the stabilising interactions suggested that there are two that play an important role: (i) hydrogen bonding between the ammonium and hydroxy groups and the acid carboxylate, which determines the formation of the columnar network and (ii) CH...π, which influences the herringbone packing of the aromatic groups, implying that it also plays some role in chiral discrimination.