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A Stereoselective Switch: Enantiodivergent Approach to the Synthesis of Isoflavanones
Author(s) -
Doran Robert,
Carroll Michael P.,
Akula Ramulu,
Hogan Bryan F.,
Martins Marta,
Fanning Séamus,
Guiry Patrick J.
Publication year - 2014
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201405246
Subject(s) - enantioselective synthesis , protonation , chemistry , stereoselectivity , modular design , aryl , stereochemistry , dual (grammatical number) , combinatorial chemistry , catalysis , organic chemistry , computer science , ion , alkyl , operating system , art , literature
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.