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Sugar ketonitrones cycloaddition

The 1,3-dipolar cycloaddition of 7V-benzyl-C-ethoxycarbonylnitrone with (5)-5-hydroxymethyl-(577)-fiiran-2-one is regio- and stereo-selective. The intramolecular 1,3-dipolar cycloaddition of sugar ketonitrones (50) provides a convenient method for the stereoselective formation of carbohydrate derivatives (51) possessing nitrogenated quaternary centres. This methodology has been successfully used to prepare synthetic precursors of (—)-tetrodotoxin (52) (Scheme 18). The hydrophobic effect has been shown to influence the rate and selectivity of 1,3-dipolar cycloaddition reactions of C,iV-diphenylnitrone with electron-deficient dipolarophiles. ... [Pg.438]

See other pages where Sugar ketonitrones cycloaddition is mentioned: [Pg.438]    [Pg.438]    [Pg.314]   
See also in sourсe #XX -- [ Pg.438 ]

See also in sourсe #XX -- [ Pg.438 ]

See also in sourсe #XX -- [ Pg.438 ]

See also in sourсe #XX -- [ Pg.97 , Pg.438 ]



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Sugar ketonitrones

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