' ) Physikalische Abteilung, Cibu-tieigy A t i , CH4002 Base1 (8.1V.92) Catalytic double osmylation is described for a series of cyclohexadienes in acetone/H,O in the presence of the co-oxidant ~'-methylmorpholine N-oxide (NMO). The formation of polyols occurred stereospecifically with cyclohexadienes 3,7, and l l a , leading thereby to tetrols 5a, and 9a and to alio-inositol(14a), respectively. To the contrary, trans-cyclohexadiene-diol 15a gave a mixture of the stereoisomeric inositols 18a (epi), 19a (nro), and 20a (chiro). High-field NMR let to clearcut conformational analyses of the polyhydroxylated derivatives.Introduction. ~ In a preliminary communication, we described the one-pot double catalytic osmylation of dihydropyridine 1 which led stereospecifically to the aminodideoxyaltrose derivative 2 [ 11. The stereospecific 'cisltranslcisltrans' outcome of this multistep reaction -which led in good yield to 5 asymmetric centres ~ is most probably due to minimization of steric interactions during each osmylation step. Due to the strong anomeric effect, which is more pronounced in piperidinoses than in pyranoses, compound 2 occurred exclusively in the chair conformation [ 11.
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