797761-89-8Relevant academic research and scientific papers
Synthesis and preparative resolution of the trans-cyclohexane analogues of phenylalanine
Cativiela, Carlos,Lopez, Pilar,Lasa, Marta
, p. 3898 - 3908 (2004)
Different approaches to the synthesis of enantiomerically pure (1R,2S)- and (1S,2R)-1-amino-2-phenylcyclohexanecarboxylic acids (trans-c6Phe) through a racemic pathway followed by semi-preparative HPLC of a racemic precursor have been studied. The complete diastereoselectivity of the Strecker reaction and the high efficiency of the subsequent transformations into the amino acid favour this method in comparison to the Diels-Alder route. The relative stereochemistry of the amino acid and its precursors has been unambiguously assigned. The preparation of the final enantiomerically pure amino acids and their corresponding N-Boc derivatives was carried out by HPLC resolution of one of the intermediates using a cellulose-derived chiral stationary phase. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.
