Selective synthesis of 3-hydroxy acids from Meldrum's acids using SmI2-H2O.

Michal Szostak, Malcolm Spain, David J Procter

Nature protocols 2012 Apr 26

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The single-step synthesis of 3-hydroxy carboxylic acids from readily available Meldrum's acids involves a selective monoreduction using a SmI(2)-H(2)O complex to give products in high crude purity, and it represents a considerable advancement over other methods for the synthesis of 3-hydroxy acids. The protocol includes a detailed guide to the preparation of a single electron-reducing SmI(2)-H(2)O complex and describes two representative examples of the methodology: monoreduction of a fully saturated Meldrum's acid (5-(4-bromobenzyl)-2,2-dimethyl-1,3-dioxane-4,6-dione) and tandem conjugate reduction-selective monoreduction of α,β-unsaturated Meldrum's acid (5-(4-methoxybenzylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione). The protocol for selective monoreduction of Meldrum's acids takes ∼6 h to complete.

Citation

Michal Szostak, Malcolm Spain, David J Procter. Selective synthesis of 3-hydroxy acids from Meldrum's acids using SmI2-H2O. Nature protocols. 2012 Apr 26;7(5):970-7