Synthesis of Chiral CF3‐Contaning Pinane‐Type Hydroxythiols

For the first time, the isomeric trifluoromethylated thioacetates have been synthesized in 37–52 % yields by nucleophilic addition of the Ruppert‐Prakash reagent (TMSCF3) to the corresponding thioacetates based on (1R)‐(−)‐myrtenal and (1S)‐(−)‐verbenone. Thioacetates have been transformed into the...

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Bibliographic Details
Published in:ChemistrySelect (Weinheim) 2021-02, Vol.6 (7), p.1710-1714
Main Authors: Ilchenko, Nikita O., Sudarikov, Denis V., Slepukhin, Pavel A., Rubtsova, Svetlana A., Kutchin, Alexandr V.
Format: Article
Language:English
Subjects:
asymmetric synthesis
Ruppert-Prakash reagent
terpenoids
thioacetate
thiol
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Summary:For the first time, the isomeric trifluoromethylated thioacetates have been synthesized in 37–52 % yields by nucleophilic addition of the Ruppert‐Prakash reagent (TMSCF3) to the corresponding thioacetates based on (1R)‐(−)‐myrtenal and (1S)‐(−)‐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. The synthesis of new chiral trifluoromethylated monoterpenic pinane‐type thiols from commercially available myrtenal and verbenone is reported. The stereochemical features and optimization of conditions of the Ruppert‐Prakash reagent addition reaction to carbonyl compounds containing thioacetate groups are discussed.
ISSN:2365-6549
2365-6549
DOI:10.1002/slct.202002657