Synthesis of Hydroxypiperidines Using 1,4-Ditosyltetrahydropyridines

What is it about?

Dihydroxylation of diastereomerically pure 2-alkyl 1,4-ditosyl-1,2,3,4-tetrahydropyridines occurs with complete stereoselectivity to give the corresponding diols. Upon treatment with nucleophile-Lewis acid mixtures the derived diacetates undergo substitution reactions whose selectivity varies according to the steric bulk of the alkyl substituent.

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