Enantioselective Synthesis of trans ‐2,3‐Dihydro‐1 H ‐indoles Through C–H Insertion of α‐Diazocarbonyl Compounds

A stereoselective synthesis of 2,3‐dihydro‐1 H ‐indoles with a Rh II ‐catalyzed C–H insertion is reported. The α‐diazo carbonyl intermediates can be obtained by a diazo‐transfer reaction of 2‐aminophenylacetic acids. Optimization and kinetic studies were performed, which resulted to increased yields...

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Bibliographic Details
Published in:European journal of organic chemistry 2017-04, Vol.2017 (14), p.1889-1893
Main Authors: Santi, Micol, Müller, Simon T. R., Folgueiras‐Amador, Ana A., Uttry, Alexander, Hellier, Paul, Wirth, Thomas
Format: Article
Language:English
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Summary:A stereoselective synthesis of 2,3‐dihydro‐1 H ‐indoles with a Rh II ‐catalyzed C–H insertion is reported. The α‐diazo carbonyl intermediates can be obtained by a diazo‐transfer reaction of 2‐aminophenylacetic acids. Optimization and kinetic studies were performed, which resulted to increased yields of the diazo transfer after mechanistic evaluation of the side‐product formation. trans ‐2,3‐Dihydro‐1 H ‐indoles were obtained in high diasteromeric excesses (up to 94 % de ) and enantiomeric excesses (up to 94 % ee ).
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201700412