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Synthesis of Chiral CF 3 ‐Contaning Pinane‐Type Hydroxythiols
Author(s) -
Ilchenko Nikita O.,
Sudarikov Denis V.,
Slepukhin Pavel A.,
Rubtsova Svetlana A.,
Kutchin Alexandr V.
Publication year - 2021
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.202002657
Subject(s) - reagent , chemistry , nucleophile , organic chemistry , nucleophilic addition , enantioselective synthesis , chiral auxiliary , stereochemistry , catalysis
For the first time, the isomeric trifluoromethylated thioacetates have been synthesized in 37–52 % yields by nucleophilic addition of the Ruppert‐Prakash reagent (TMSCF 3 ) to the corresponding thioacetates based on (1 R )‐(−)‐myrtenal and (1 S )‐(−)‐verbenone. Thioacetates have been transformed into the corresponding pinane thiols in 73–90 % yields. The structure and configuration of the resulting compounds have been determined.