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Chemoenzymatic Synthesis of Enantiomerically Pure syn ‐Configured 1‐Aryl‐3‐methylisochroman Derivatives
Author(s) -
Simon Robert C.,
Busto Eduardo,
Richter Nina,
Belaj Ferdinand,
Kroutil Wolfgang
Publication year - 2014
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201301429
Subject(s) - enantiopure drug , chemistry , diastereomer , enantioselective synthesis , ketone , aryl , alcohol , enantiomer , yield (engineering) , enantiomeric excess , biocatalysis , stereochemistry , organic chemistry , catalysis , reaction mechanism , alkyl , materials science , metallurgy
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 by biocatalytic reduction by employing enantiocomplementary alcohol dehydrogenases, which gave access to the ( S ) and ( R ) enantiomer with up to >99 % conversion and up to >99 % ee .