84580-99-4Relevant academic research and scientific papers
Stereoselective Synthesis of 1-Arylpropan-2-amines from Allylbenzenes through a Wacker-Tsuji Oxidation-Biotransamination Sequential Process
González-Martínez, Daniel,Gotor, Vicente,Gotor-Fernández, Vicente
, p. 2582 - 2593 (2019/05/15)
Herein, a sequential and selective chemoenzymatic approach is described involving the metal-catalysed Wacker-Tsuji oxidation of allylbenzenes followed by the amine transaminase-catalysed biotransamination of the resulting 1-arylpropan-2-ones. Thus, a series of nine optically active 1-arylpropan-2-amines were obtained with good to very high conversions (74–92%) and excellent selectivities (>99% enantiomeric excess) in aqueous medium. The Wacker-Tsuji reaction has been exhaustively optimised searching for compatible conditions with the biotransamination experiments, using palladium(II) complexes as catalysts and iron(III) salts as terminal oxidants in aqueous media. The compatibility of palladium/iron systems for the chemical oxidation with commercially available and made in house amine transaminases was analysed, finding ideal conditions for the development of a general and stereoselective cascade sequence. Depending on the selectivity displayed by selected amine transaminase, it was possible to produce both 1-arylpropan-2-amines enantiomers under mild reaction conditions, compounds that present therapeutic properties or can be employed as synthetic intermediates of chiral drugs from the amphetamine family. (Figure presented.).
Enzymatic enantiomeric resolution of phenylethylamines structurally related to amphetamine
Munoz, Lourdes,Rodriguez, Anna M.,Rosell, Gloria,Bosch, M. Pilar,Guerrero, Angel
, p. 8171 - 8177 (2012/01/04)
Both enantiomers of several phenylethylamines, structurally related to amphetamine, have been prepared in good yields and excellent enantiomeric purity by enzymatic kinetic resolution using CAL-B and ethyl methoxyacetate as the acyl donor. In the case of the 4-hydroxyderivative of amphetamine (compound 4i), the S enantiomer racemized possibly in a dynamic kinetic resolution (DKR) under the enzymatic conditions used. The Royal Society of Chemistry 2011.
Optically Active Amines. 31. Spectral Observations on the Substituted Benzene Chromophore
Smith, Howard E.,Neergaard, Jon R.,Paulis, Tomas de,Chen, Fu-Ming
, p. 1578 - 1584 (2007/10/02)
Examination of the isotropic absorption and circular dichroism spectra of para-substituted and 3,5-disubstituted α-phenyl- and α-benzylethylamines and their hydrochlorides indicates that the sign of 1Lb Cotton effects (CEs) of the be
