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A protocol for the stereodivergent pentafluoroethylation of -sulfinylimines using HFC-125 with KHMDS/triglyme has been developed. Both diastereomers of the pentafluoroethylated amines can be selectively synthesized based on the presence or absence of triglyme. This additive-controlled protocol allows the KHMDS/triglyme cryptate to be a straightforward and cheap alternative to previously reported base-controlled stereodivergent trifluoromethylation using potassium hexamethyldisilazide (KHMDS) versus P-Bu.
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| http://dx.doi.org/10.1021/acs.joc.2c01821 | DOI Listing |
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KHMDS/Triglyme Cryptate as an Alternative to Phosphazene Base in Stereodivergent Pentafluoroethylation of -Sulfinylimines Using HFC-125.
J Org Chem
December 2022
Department of Life Science and Applied Chemistry, Nagoya Institute of Technology, Gokiso, Showa-Ku, Nagoya 466-8555, Japan.
A protocol for the stereodivergent pentafluoroethylation of -sulfinylimines using HFC-125 with KHMDS/triglyme has been developed. Both diastereomers of the pentafluoroethylated amines can be selectively synthesized based on the presence or absence of triglyme. This additive-controlled protocol allows the KHMDS/triglyme cryptate to be a straightforward and cheap alternative to previously reported base-controlled stereodivergent trifluoromethylation using potassium hexamethyldisilazide (KHMDS) versus P-Bu.
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