Studies on cyclitols—XVII

Powell, Keith; Hughes, AD; Katchian, H.; Jerauld, J. F.; Sable, Henry Z.

doi:10.1016/0040-4020(72)88010-4

Cited by 14 publications

(7 citation statements)

References 15 publications

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“…Hax-C(6) Hea+ (6) ') The pseudo-chair conformation A is also corroborated by the J( 1,2), J(2,3), and J(2,4) coupling constants (see Table 1 ) . For similar half-chair conformations, see [13-151.…”

Section: <->supporting

confidence: 55%

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Catalytic One‐Pot Osmylation of Cyclohexadienes: Stereochemical and conformational studies of the resulting polyols

Tschamber

Backenstrass

Fritz

et al. 1992

Helvetica Chimica Acta

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' ) 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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Section: <->supporting

confidence: 55%

“…The stereochemical outcome of this latter reaction was explained by assuming a 'cis-complexation' of both double bonds by KMnO, followed by an 'anti'-hydrolysis of the so-formed 'manganic ester' [S]. As to the double hydroxylation of diene 7 with KMnO,, it gave a mixture 8a/9a, both in poor yield [6]. Eventually, McCuslund et a/.…”

mentioning

confidence: 98%

Catalytic One‐Pot Osmylation of Cyclohexadienes: Stereochemical and conformational studies of the resulting polyols

Tschamber

Backenstrass

Fritz

et al. 1992

Helvetica Chimica Acta

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“…No diepoxide was observed despite treatment with a slight excess of MCPBA. Dihydroxylation with OsO 4 -NMO gives, after isolation by continuous extraction, epoxydiol 8 12 (73%). Protection of epoxydiol 8 with TBDMSCl gives epoxide 7 in near quantitative yield.…”

Section: Resultsmentioning

confidence: 99%

Functionalised bicyclic alcohols by enantioselective α-deprotonation–rearrangement of meso-epoxides†

Hodgson

Cameron

Christlieb

et al. 2001

J. Chem. Soc., Perkin Trans. 1

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“…The mixture was evaporated and the residue was chromatographed over silica gel (eluent: water/ethanol/ ethyl acetate 1:2:5) to afford tetrol (2) (97%) (Kawazoe et al, 2001). Tetrol (2) was acetylated as described in the literature (Powell et al, 1972). Recrystallization of compound (3) from dichloromethane/ hexane (1:3) gave colourless crystals of (3) (m.p.…”

Section: Methodsmentioning

confidence: 99%