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Synfacts 2014; 10(3): 0285
DOI: 10.1055/s-0033-1340695
DOI: 10.1055/s-0033-1340695
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
Asymmetric Arylation of α-Keto Esters by Rhodium Catalysis
Li Y, Zhu D.-X, Xu M.-H * Shanghai Institute of Materia Medica, P. R. of China
A New Versatile Approach to Synthesise Enantioenriched 3-Hydroxyoxindoles, 1,3-Dihydroisobenzofuran and 3-Isochromanone Derivatives by a Rhodium-Catalyzed Asymmetric Arylation–Cyclization Sequence.
Chem. Commun. 2013;
49: 11659-11661
A New Versatile Approach to Synthesise Enantioenriched 3-Hydroxyoxindoles, 1,3-Dihydroisobenzofuran and 3-Isochromanone Derivatives by a Rhodium-Catalyzed Asymmetric Arylation–Cyclization Sequence.
Chem. Commun. 2013;
49: 11659-11661
Further Information
Publication History
Publication Date:
17 February 2014 (online)
Significance
The authors describe a rhodium-catalyzed enantioselective arylation of ortho-substituted aryl α-keto esters with arylboronic acids, delivering highly functionalized quaternary α-hydroxy esters in good yield (up to 90%) and high enantiomer excess (up to 98%). The success of the new sulfur-based olefin ligands L1 and L2 for sterically challenging substrates is intriguing.
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Comment
The arylation strategy was efficiently coupled with a cyclization process and depending on the ortho-substitution of the keto ester chiral derivatives of 3-hydroxyoxindole, 1,3-dihydroisobenzofuran, and 3-isochromanone were synthesized. These compounds are pharmaceutically attractive.
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