ウロース類に対する求核反応の立体選択性

概要

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Stereoselectivities in the nucleophilic addition of various nucleophiles to various 2-, 3-, 4-uloses were examined, and discussions were made on the possible, conformational change of substrates and on the following, three, main factors to control the stereoselectivities depending on the nature of reactions ; a) non-bonded interactions, after the preceding, conformational change by the coordination of magnesium to the C=O and adjacent C-O oxygens (methylmagnesium iodide) or by the solvent-dependent, dipole repulsion between the C=O and C-O bonds (methyllithium), b) intramolecular, electrostatic, attractive force between an axial oxygen or lone-paired electron of ringoxygen and diazomethyl cation in the transition states (diazomethane), c) thermodynamical stabilities of epimers to be produced in equilibration reaction.
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