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Enantioselective synthesis of trans-2,3-Dihydro-1H-indoles through C-H Insertion of a-Diazocarbonyl compounds

Santi, Micol, Müller, Simon T. R., Folgueiras-Amador, Ana, Uttry, Alexander, Hellier, Paul and Wirth, Thomas 2017. Enantioselective synthesis of trans-2,3-Dihydro-1H-indoles through C-H Insertion of a-Diazocarbonyl compounds. European Journal of Organic Chemistry 2017 (14) , pp. 1889-1893. 10.1002/ejoc.201700412

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Abstract

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).

Item Type: Article
Date Type: Publication
Status: Published
Schools: Chemistry
Subjects: Q Science > QD Chemistry
Uncontrolled Keywords: Diazo compounds; Azides; Dihydroindole; C–H insertion; Rhodium
Publisher: Wiley
ISSN: 1434-193X
Funders: Pierre Fabre
Date of First Compliant Deposit: 29 March 2017
Date of Acceptance: 23 March 2017
Last Modified: 24 Aug 2020 13:58
URI: http://orca-mwe.cf.ac.uk/id/eprint/99482

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