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- Title
Chemoenzymatic Synthesis of Enantiomerically Pure syn-Configured 1-Aryl-3-methylisochroman Derivatives.
- Authors
Simon, Robert C.; Busto, Eduardo; Richter, Nina; Belaj, Ferdinand; Kroutil, Wolfgang
- 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 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.
- Subjects
CHEMICAL derivatives; PICTET-Spengler reaction; DIASTEREOISOMERS synthesis; BOND formation mechanism; DEHYDROGENASES; DEHYDROGENATION
- Publication
European Journal of Organic Chemistry, 2014, Vol 2014, Issue 1, p111
- ISSN
1434-193X
- Publication type
Article
- DOI
10.1002/ejoc.201301429