Chemoenzymatic Synthesis of Enantiomerically Pure syn??Configured 1??Aryl??3??methylisochroman Derivatives

RC Simon, E Busto, N Richter, F Belaj…

Index: Simon, Robert C.; Busto, Eduardo; Richter, Nina; Belaj, Ferdinand; Kroutil, Wolfgang European Journal of Organic Chemistry, 2014 , vol. 2014, # 1 p. 111 - 121

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Citation Number: 8

Abstract

Abstract A two-step synthesis of various enantiomerically pure 1-aryl-3-methylisochroman derivatives was accomplished through asymmetric biocatalytic ketone reduction followed by an oxa-Pictet–Spengler reaction. The compounds were obtained in good to excellent yield (47–92%) in favor of the syn diastereomers [dr (syn/anti) up to 99: 1]. Enantiopure arylpropanols serving as pronucleophiles for the C–C bond-formation step were obtained ...