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- Title
Synthesis of Trifluoromethylated Monoterpene Amino Alcohols.
- Authors
Petrova, Polina A.; Sudarikov, Denis V.; Frolova, Larisa L.; Rumyantcev, Roman V.; Rubtsova, Svetlana A.; Kutchin, Aleksandr V.
- Abstract
For the first time, monoterpene trifluoromethylated β-hydroxy-benzyl-O-oximes were synthesized in 81–95% yields by nucleophilic addition of the Ruppert–Prakash reagent (TMSCF3) to the corresponding β-keto-benzyl-O-oximes based on (+)-nopinone, (−)-verbanone and (+)-camphoroquinone. Trifluoromethylation has been determined to entirely proceed chemo- and stereoselective at the C=O rather than C=N bond. Trifluoromethylated benzyl-O-oximes were reduced to the corresponding α-trifluoromethyl-β-amino alcohols in 82–88% yields. The structure and configuration of the compounds obtained have been established.
- Subjects
MONOTERPENES; AMINO alcohols; ALCOHOL; MONOTERPENOIDS
- Publication
Molecules, 2022, Vol 27, Issue 20, p7068
- ISSN
1420-3049
- Publication type
Article
- DOI
10.3390/molecules27207068