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KHMDS/Triglyme Cryptate as an Alternative to Phosphazene Base in Stereodivergent Pentafluoroethylation of N-Sulfinylimines Using HFC-125.
Yuji Sumii
1 ,
Hiroto Iwasaki
1 ,
Yamato Fujihira
1 ,
Elsayed M Mahmoud
2
,
3 ,
Hiroaki Adachi
4 ,
Takumi Kagawa
4 ,
Dominique Cahard
5 ,
Norio Shibata
1
,
2
Dec 02 2022
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Abstract
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-tBu.