Tetrahedron p. 3481 - 3490 (1984)
Update date:2022-08-05
Topics:
Masaki, Yukio
Hashimoto, Kinji
Kaji, Kenji
Highly site- and regioselective terminal functionalizations of acyclic monoterpenes 1 via benzenesulfenyl chloride addition followed by hydrolysis assisted by silica gel, dehydrochlorination under neutral or weakly basic condition, or dehydrochlorination by strongly basic treatment respectively providing β-hydroxy sulfides 3, terminal methallylic sulfides 4, or vinylsulfides 5 are developed.Conversion of 4 to terminal trans-allylic alcohols 10 via sulfoxides 9 by the Evans procedure is also described.
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(1992)
