156942-67-5Relevant articles and documents
New Chiral Anisotropic Reagents, NMR Tools to Elucidate the Absolute Configuration of Long-chain Organic Compounds
Kusumi, Takenori,Takahashi, Haruko,Xu, Ping,Fukusima, Toshiro,Asakawa, Yoshinori,et al.
, p. 4397 - 4400 (1994)
Modified Mosher's method has been extended by use of 9-anthranylmethoxyacetic acid (9ATMA) and 2-naphthylmethoxynaphthylacetic acid (2NMA) instead of MTPA of the conventional method.Anisotropic effects of these reagents are much greater than that of MTPA, and the reagents have been shown to useful especially to determine the absolute configurations of the secondary alcohols involved in long-chain componds.
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.
Chemo-enzymatic synthesis of enantiomerically pure (R)-2-naphthylmethoxyacetic acid
Kimura, Mayumi,Kuboki, Atsuhito,Sugai, Takeshi
, p. 1059 - 1068 (2007/10/03)
Enantiomerically pure (R)-2-naphthylmethoxyacetic acid (2-NMA) was synthesized from 2-naphthaldehyde via an integrated chemo-enzymatic procedure. The one-pot, successive use of SnBr2-TMSCN and AcBr worked effectively to give a racemic cyanohydrin acetate. Lipase from Burkholderia cepacia then mediated the highly enantioselective hydrolysis of the (S)-enantiomer of the racemate, leaving the (R)-acetate with an e.e. of >99.9%. The resulting product of this enzyme-catalyzed hydrolysis, an (S)-cyanohydrin, spontaneously decomposed into naphthaldehyde, the starting material of this synthetic route, which could be recycled. The hydration of nitrile to amide as well as the hydrolysis of the acetate was performed with a microorganism, Rhodococcus rhodochrous, under very mild conditions without any loss of the enantiomeric purity. The amide group was hydrolyzed with nitrosylsulfuric acid, and the product was isolated as an α-hydroxy ester. The α-hydroxyl group was methylated with diazomethane-silica gel and the final task, hydrolysis of the ester, was accomplished under conditions as mild as neutral pH with an esterase from Krebsiella oxytoca to give enantiomerically pure 2-NMA.
Conformational Structure and Dynamics of Arylmethoxyacetates: DNMR Spectroscopy and Aromatic Shielding Effect
Latypov, Sh. K.,Seco, J. M.,Quinoa, E.,Riguera, R.
, p. 504 - 515 (2007/10/02)
The ground state conformational geometry and energy of esters of (R)- and (S)-arylmethoxyacetic acids were evaluated from low temperature 1H and 13C NMR spectra and by means of MM, AM1, and aromatic shielding effect calculations.In solution, the title com
