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Despite the ubiquitous use of phosphoramidite chemistry in the synthesis of biophosphates, catalytic asymmetric phosphoramidite transfer remains largely unexplored for phosphate ester synthesis. We have discovered that a tetrazole-functionalized peptide, in the presence of 10-Å molecular sieves, functions as an enantioselective catalyst for phosphite transfer. This chemistry in turn has been used as the key step in a streamlined synthesis of myo-inositol-6-phosphate. Mechanistic insights implicate phosphate as a directing group for a highly selective kinetic resolution of a protected inositol monophosphate. This work represents a distinct and efficient method for the selective catalytic phosphorylation of natural products.

proceedings of the national academy of sciences of the united states of america

Asymmetric phosphorylation through catalytic P(III) phosphoramidite transfer: Enantioselective synthesis of <scp>d</scp> - <i>myo</i> -inositol-6-phosphate

Asymmetric phosphorylation through catalytic P(III) phosphoramidite transfer: Enantioselective synthesis of d - myo -inositol-6-phosphate