Asymmetric Cu1-Catalyzed Insertion Reaction of 1-Aryl-2,2,2- trifluoro-1-diazoethanes into Si–H Bonds

Authors: Carreras, VirginieBesnard, Claire; Gandon, Vincent; Ollevier, Thierry
Abstract: An asymmetric copper(I)-catalyzed Si−H insertion reaction of 1-aryl-2,2,2-trifluoro-1-diazoethanes in dimethyl carbonate as a green solvent alternative was developed. A C2-symmetric copper(I) diimine complex enabled the asymmetric insertion reaction to give enantioenriched (1-aryl-2,2,2-trifluoroethyl)silanes with excellent stereoselectivities (up to 98:2 er). Successful conversion of the silanes into the corresponding alcohols was performed with retention of stereochemistry. Mechanistic studies and DFT calculations support the proposed model for the observed stereoselectivities.
Document Type: Article de recherche
Issue Date: 28 October 2019
Open Access Date: 28 October 2020
Document version: AM
Permalink: http://hdl.handle.net/20.500.11794/37481
This document was published in: Organic letters, Vol. 21 (22), 9094-9098 (2019)
https://doi.org/10.1021/acs.orglett.9b03480
American Chemical Society
Alternative version: 10.1021/acs.orglett.9b03480
31657938
Collection:Articles publiés dans des revues avec comité de lecture

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