A MECHANISTICALLY DESIGNED BIS-CINCHONA ALKALOID LIGAND ALLOWS POSITION-SELECTIVE AND ENANTIOSELECTIVE DIHYDROXYLATION OF FARNESOL AND OTHER OLIGOPRENYL DERIVATIVES AT THE TERMINAL ISOPROPYLIDENE UNIT

被引：76

作者：

COREY, EJ

NOE, MC

LIN, SZ

机构：

[1] Department of Chemistry, Harvard University, Cambridge, Massachusetts

来源：

TETRAHEDRON LETTERS | 1995年 / 36卷 / 48期

关键词：

D O I：

10.1016/0040-4039(95)01920-D

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The mechanistically designed bis-cinchona alkaloid derivative 3 serves as an excellent catalytic ligand in the OsO4-promoted catalytic enantioselective dihydroxylation of the terminal isopropylidene group in farnesyl, geranylgeranyl, and solanesyl esters and also squalene, with selectivity as high as 120:1 with E,E-farnesyl acetate. H-1 NMR and X-ray studies support the conformation described by 3 in which the U-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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页码：8741 / 8744

页数：4

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