title: Selective synthesis of 3-hydroxy acids from Meldrum's acids using SmI2-H2O.
abstract: 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.
authors.affiliation: School of Chemistry, University of Manchester, UK.
authors.forename: Michal
authors.initials: M
authors.lastname: Szostak
authors.forename: Malcolm
authors.initials: M
authors.lastname: Spain
authors.forename: David J
authors.initials: DJ
authors.lastname: Procter
mesh_terms: D002625:Chemistry, Organic / Q000379:methods*; D004146:Dioxanes / Q000737:chemistry*; D006880:Hydroxy Acids / Q000138:chemical synthesis*; D007454:Iodides / Q000737:chemistry*; D012493:Samarium / Q000737:chemistry*; D014867:Water / Q000737:chemistry*
chemical_list: D004146:Dioxanes; D006880:Hydroxy Acids; D007454:Iodides; D014867:Water; D012493:Samarium; C076489:Meldrum's acid; C409809:samarium diiodide