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Ruthenium‐Catalyzed Asymmetric Alkene Epoxidation with tert ‐Butyl Hydroperoxide as Oxidant
Author(s) -
Bhor Santosh,
Tse Man Kin,
Klawonn Markus,
Döbler Christian,
Mägerlein Wolfgang,
Beller Matthias
Publication year - 2004
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.200303142
Subject(s) - chemistry , chemoselectivity , ruthenium , catalysis , tert butyl hydroperoxide , alkene , yield (engineering) , stoichiometry , organic chemistry , medicinal chemistry , materials science , metallurgy
A ruthenium‐catalyzed asymmetric epoxidation of various olefins using tert ‐butyl hydroperoxide (TBHP) as the oxidant is reported. By applying ruthenium(pyridinebisoxazoline)‐(pyridinedicarboxylate) complexes 1 [Ru(pybox)(pydic), 1 ] as catalysts, aromatic and aliphatic olefins yielded the corresponding epoxides at room temperature in good to excellent yields and enantioselectivities up to 65% ee. Slow addition of the stoichiometric oxidant significantly improved the yield and the chemoselectivity of the reaction.