Synthesis of Chiral CF 3 ‐Contaning Pinane‐Type Hydroxythiols | Zendy

Ilchenko Nikita O. | Zendy; Sudarikov Denis V. | Zendy; Slepukhin Pavel A. | Zendy; Rubtsova Svetlana A. | Zendy; Kutchin Alexandr V. | Zendy

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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.

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