Journal
ORGANIC LETTERS
Volume 21, Issue 22, Pages 9094-9098Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.9b03480
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Funding
- Natural Sciences and Engineering Research Council of Canada (NSERC) [RGPIN-2017-04272]
- FRQNT Centre in Green Chemistry and Catalysis (CGCC) Strategic Cluster [FRQNT-2020-RS4-265155-CCVC]
- Universite Laval
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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 C-2-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.
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