A stereoselective switch: enantiodivergent approach to the synthesis of isoflavanones
Robert Doran1, Michael P Carroll, Ramulu Akula
1Centre for Synthesis and Chemical Biology, School of Chemistry and Chemical Biology, University College Dublin, Belfield, Dublin 4 (Ireland).
Abstract:
A modular six-step asymmetric synthesis of two naturally occurring and three non-natural isoflavanones containing tertiary α-aryl carbonyls is reported. This synthetic route, utilising a Pd-catalyzed decarboxylative asymmetric protonation, produces isoflavanones in excellent enantioselectivities from 76-97 %. A switch in the sense of stereoinduction was observed when different H(+) sources were employed, showing the first example of dual stereocontrol in an asymmetric protonation reaction. The first enantioselective synthesis of the naturally occurring isoflavanones sativanone and 3-o-methylviolanone has been accomplished.
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