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A Stereoselective Switch: Enantiodivergent Approach to the Synthesis of Isoflavanones

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.

Proton Haze—Don′t know if I′m comin’ up or down: The first asymmetric synthesis of the naturally occurring isoflavanones, sativanone and 3‐O‐methylviolanone, containing tertiary α‐aryl carbonyls, has been accomplished. This was achieved through a Pd‐catalyzed decarboxylative asymmetric protonation in excellent enantioselectivities from 76–97 %. A switch in the sense of stereoinduction was observed when different H+ sources were employed.

Autoren:   Robert Doran, Michael P. Carroll, Ramulu Akula, Bryan F. Hogan, Marta Martins, Séamus Fanning, Patrick J. Guiry
Journal:   Chemistry - A European Journal
Jahrgang:   2014
Seiten:   n/a
DOI:   10.1002/chem.201405246
Erscheinungsdatum:   14.10.2014
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