A mechanistically designed bis-cinchona alkaloid ligand allows position- and enantioselective dihydroxylation of farnesol and other oligoprenyl derivatives at the terminal isopropylidene unit
摘要:
The mechanistically designed bis-cinchona alkaloid derivative 3 serves as an excellent catalytic ligand in the OsO 4 -promoted catalytic enantioselective dihydroxylation of the terminal isopropylidene group infamesyl, geranylgeranyl, and solanesyl esters and also squalene, with selectivity as high as 120: 1 with E,E-farnesyl acetate. 1 H NMR and X-ray studies support the conformation described by 3 in which the V-shaped catalytic binding pocket is composed of the two 6-(4-heptyloxy)-quinoline units (sides and rear) and the naphthopyridazine linker (bottom).
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DOI:
10.1016/0040-4039(95)01920-D
被引量:
年份:
1995
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