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

Autor:	Alexander Uttry, Paul Hellier, Thomas Wirth, Micol Santi, Ana A. Folgueiras-Amador, Simon T. R. Müller
Rok vydání:	2017
Předmět:	010405 organic chemistry Stereochemistry Organic Chemistry Enantioselective synthesis 010402 general chemistry 01 natural sciences 0104 chemical sciences chemistry.chemical_compound chemistry Organic chemistry Diazo Stereoselectivity Physical and Theoretical Chemistry Enantiomer
Zdroj:	European Journal of Organic Chemistry. 2017:1889-1893
ISSN:	1434-193X
DOI:	10.1002/ejoc.201700412
Popis:	A stereoselective synthesis of 2,3-dihydro-1H-indoles with a RhII-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-1H-indoles were obtained in high diasteromeric excesses (up to 94 % de) and enantiomeric excesses (up to 94 % ee).
Databáze:	OpenAIRE
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