KHMDS/Triglyme Cryptate as an Alternative to Phosphazene Base in Stereodivergent Pentafluoroethylation of N‑Sulfinylimines Using HFC-125

A protocol for the stereodivergent pentafluoroethylation of N-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 allo...

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Bibliographic Details
Published inJournal of organic chemistry Vol. 87; no. 23; pp. 15806 - 15819
Main Authors Sumii, Yuji, Iwasaki, Hiroto, Fujihira, Yamato, Mahmoud, Elsayed M., Adachi, Hiroaki, Kagawa, Takumi, Cahard, Dominique, Shibata, Norio
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 02.12.2022
American Chemical Society (ACS)
Amer Chemical Soc
Subjects
[CHIM.ORGA]Chemical Sciences/Organic chemistry
Chemical Sciences
Chemistry
Chemistry, Organic
Crown Ethers
Fluorocarbons
Organic chemistry
Physical Sciences
Polyethylene Glycols
Science & Technology
ASYMMETRIC FLUORINATION
KETONES
PERFLUOROALKYLATION
TRIFLUOROMETHYLATION
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ISSN0022-3263
1520-6904
1520-6904
DOI10.1021/acs.joc.2c01821

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Summary:A protocol for the stereodivergent pentafluoroethylation of N-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 P4- t Bu.
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ISSN:0022-3263
1520-6904
1520-6904
DOI:10.1021/acs.joc.2c01821