Selective synthesis of 3-hydroxy acids from meldrum’s acids using Smi2-H2o

Michal Szostak, Malcolm Spain, David J. Procter

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25 Scopus citations

Abstract

The single-step synthesis of 3-hydroxy carboxylic acids from readily available Meldrum’s acids involves a selective mono reduction using a smI2-H2O 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 smI2-H2O complex and describes two representative examples of the methodology: mono reduction of a fully saturated Meldrum’s acid (5-(4-bromobenzyl)-2, 2-dimethyl-1, 3-dioxane-4, 6-dione) and tandem conjugate reduction-selective mono reduction of a, b-unsaturated Meldrum’s acid (5-(4-methoxybenzylidene)-2, 2-dimethyl-1, 3-dioxane-4, 6-dione). The protocol for selective mono reduction of Meldrum’s acids takes ˜6 h to complete.

Original languageEnglish (US)
Pages (from-to)970-977
Number of pages8
JournalNature Protocols
Volume7
Issue number5
DOIs
StatePublished - Nov 2012
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Biochemistry, Genetics and Molecular Biology(all)

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