56031-82-4Relevant articles and documents
Traceless Silylation of β-C(sp3)-H Bonds of Alcohols via Perfluorinated Acetals
Bunescu, Ala,Butcher, Trevor W.,Hartwig, John F.
, p. 1502 - 1507 (2018/02/09)
We report the silylation of primary C-H bonds located β to secondary and tertiary alcohols by exploiting perfluorinated esters as traceless directing groups. The conversion of a secondary or tertiary alcohol to a perfluoroalkyl ester and conversion of the ester to the corresponding silyl acetals by hydrosilylation allows for selective β-C(sp3)-H silylation catalyzed by the combination of [Ir(cod)OMe]2 and Me4Phen (3,4,7,8-tetramethyl-1,10-phenanthroline) to form 6-membered dioxasilinane. Tamao-Fleming oxidation of these dioxasilinane leads to 1,2 diols. The developed sequence was applied to a series of natural products containing hydroxyl groups.
Superacidic cyclization of ω-hydroxygeraniol diacetate and ω-hydroxygeraniol benzyl ether acetate
Kulcitki,Ungur,Deleanu,Vlad
, p. 136 - 138 (2007/10/03)
Low-temperature superacidic cyclization of (E,E)-3,7-dimethylocta-2,6-diene-1,8-diol (ω-hydroxygeraniol) diacetate and (E,E)-8-acetoxy-1-benzyloxy-3,7-dimethylocta-2,6-diene leads to the same mixtures of two diastereomeric 9-acetoxy-8-hydroxy-p-menth-1-enes epimeric at the C(8) atom.
Halogenated Terpenoids. XXII. Uroterpenol. The C8 Stereochemistry
Carman, Raymond M.,Greenfield, Kay L.,Robinson, Ward T.
, p. 21 - 30 (2007/10/02)
The two diastereoisomeric p-menth-1-ene-8,9-diols (uroterpenols) have been separated and crystallized.A crystallographic analysis of a dibromo derivative enables relative and absolute configurations to be assigned throughout the series.