Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 346, Issue 12, Pages 1471-1480Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.200404112
Keywords
asymmetric synthesis; bifunctional catalysis; chiral diols; counterionic stabilization; nanocrystalline magnesium oxide
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New bifunctional catalysts composed of PdCl42-, OsO42- and OsO42-, WO42- designed and prepared by a counterionic stabilization technique involving the reactions of Na2PdCl4-K2OsO4 and K2OsO4-Na2WO4 with nanocrystalline MgO are well characterized. These bifunctional catalysts, NAP-Mg-PdOs and NAP-Mg-OsW perform tandem Heck asymmetric dihydroxylation and asymmetric dihydroxylation-N-oxidation reactions, respectively, in the presence of the chiral ligand 1,4-bis(9-o-dihydroquinidinyl)phthalazine [(DHQD)(2)PHAL] in a single pot. It is quite impressive to note that H,02 is used as a terminal oxidant to provide N-methylmorpholine N-oxide (NMO) in situ by the oxidation of N-methylmorpholine (NMM) in the asymmetric dihydroxylation-N-oxidation catalyzed by NAP-Mg-OsW.
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