Cycloalkenyl Halide Substitution Reactions of Enantiopure Arene cis-Tetrahydrodiols with Boron, Nitrogen and Phosphorus Nucleophiles.

D. R. BOYD; N. D. SHARMA; M. KAIK; M. BELL; M. V. BERBERIAN; P.B. A. MCINTYRE; B. KELLY; C. HARDACRE; P. J. STEVENSON ; C.C. R. ALLEN

ADVANCED SYNTHESIS & CATALYSIS (PRINT)

WILEY-V C H VERLAG GMBH

Año: 2011 vol. 353 p. 2455 - 2465

1615-4150

Enantiopure arene cis-tetrahydrodiols of bromobenzene and iodobenzene have been obtained in good yields, from chemoselective hydrogenation (Rh-graphite) of the corresponding cis-dihydrodiol metabolites. Palladium-catalysed substitution of the halogen group, by boron, nitrogen and phosphorus nucleophiles, and hydrogen, in the acetonide derivatives, has yielded highly functionalised products for application in synthesis with potential as scaffolds for chiral ligands.