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Enantioselective Synthesis of trans ‐2,3‐Dihydro‐1 H ‐indoles Through C–H Insertion of α‐Diazocarbonyl Compounds
Author(s) -
Santi Micol,
Müller Simon T. R.,
FolgueirasAmador Ana A.,
Uttry Alexander,
Hellier Paul,
Wirth Thomas
Publication year - 2017
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201700412
Subject(s) - chemistry , enantioselective synthesis , diazo , enantiomer , stereoselectivity , stereochemistry , formal synthesis , enantiomeric excess , catalysis , medicinal chemistry , organic chemistry
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 ).