Document Detail


Selective synthesis of 3-hydroxy acids from Meldrum's acids using SmI(2)-H(2)O.
MedLine Citation:
PMID:  22538848     Owner:  NLM     Status:  In-Data-Review    
Abstract/OtherAbstract:
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:
Michal Szostak; Malcolm Spain; David J Procter
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Publication Detail:
Type:  Journal Article     Date:  2012-04-26
Journal Detail:
Title:  Nature protocols     Volume:  7     ISSN:  1750-2799     ISO Abbreviation:  Nat Protoc     Publication Date:  2012  
Date Detail:
Created Date:  2012-04-27     Completed Date:  -     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  101284307     Medline TA:  Nat Protoc     Country:  England    
Other Details:
Languages:  eng     Pagination:  970-7     Citation Subset:  IM    
Affiliation:
School of Chemistry, University of Manchester, Manchester, UK.
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