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Asymmetric epoxidation of styrene and chromenes catalysed by chiral (salen)Mn(III) complexes with a pyrrolidine backbone

Wang, D. P. (author)
Wang, M. (author)
Wang, X. N. (author)
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Chen, Y. G. (author)
Gao, A. P. (author)
Sun, Licheng C. (author)
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Elsevier BV, 2006
2006
English.
In: Journal of Catalysis. - : Elsevier BV. - 0021-9517 .- 1090-2694. ; 237:2, s. 248-254
  • Journal article (peer-reviewed)
Abstract Subject headings
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  • A series of chiral (pyrrolidine salen)Mn(III) complexes were synthesized front N-aza-substituted (R,R)-N,N'-bis(3,5-di-tert-butylsalicylidene)-3.4-diaminopyrrolidine salen ligands. High yields and comparable enantioselectivity relative to Jacobsen's catalyst were achieved in asymmetric epoxidation of styrene and chromenes using NaClO/PPNO and m-CPBA/NMO as the oxidant systems. Complexes 1-3, featuring a tertiary airline unit, displayed higher activity than complex 4, bearing ail amide unit and Jacobsen's catalyst in the NaClO/PPNO aqueous/organic biphasic system. The influence of CH3I on epoxidation of 6-nitro-2,2-dimethylchromene catalysed by 1-4 in the biphasic medium was Studied to explore the catalysts with built-in phase-transfer capability. The alkenes' access pathway is discussed on the basis of the steric effect of the N-aza-substituent in the pyrrolidine backbone of complexes 1-3 on the enantioselectivity of epoxidation.

Keyword

asymmetric epoxidation
enantioselectivity
pyrrolidine
(salen)Mn(III) complex
unfunctionalized alkenes
active (salen)manganese(iii) complexes
phase-transfer capability
enantioselective epoxidation
nonfunctionalized alkenes
salen complexes
olefins

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