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Terpenyl Selenides: Synthesis and Application in Asymmetric Epoxidation
Author(s) -
Banach Anna,
Ścianowski Jacek,
UzarewiczBaig Magdalena,
Wojtczak Andrzej
Publication year - 2015
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201500211
Subject(s) - chemistry , limonene , menthol , diastereomer , organic chemistry , solvent , monoterpene , chromatography , essential oil
Synthesis of terpenyl selenides derived from limonene, menthol, caranol, and myrtanol is described. Three methodologies for the synthesis of terpenyl selenonium salts are compared. The results of selenium‐mediated epoxidation through the use of isoselenocineole derived from limonene and methyl terpenyl, phenyl terpenyl, diterpenyl selenides, and selenonium salts are presented. The influence of solvent, counteranion, and diastereomeric purity of selenonium salt on the enantioselectivity of the epoxidation reaction is discussed.