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Synthesis 2012; 44(23): 3633-3638
DOI: 10.1055/s-0032-1317509
DOI: 10.1055/s-0032-1317509
paper
Samarium Diiodide Mediated Highly Diastereoselective Conjugate Reduction of the α,β-Unsaturated Ester Moiety in Heterocyclic Compounds
Further Information
Publication History
Received: 12 August 2012
Accepted after revision: 07 October 2012
Publication Date:
05 November 2012 (online)
Abstract
Tetrahydropyrazolopyrazolones and a tetrahydropyrazolodiazocinone containing an α,β-unsaturated ester moiety undergo highly diastereoselective conjugate reduction mediated by samarium diiodide in the mixed solvent tetrahydrofuran and ethanol to give the corresponding products as single diastereomers in moderate to good yields.
Supporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
- Supporting Information
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For several reviews, see:
For selected examples, see:
For selected examples about SmI2-mediated reductions, see:
About the reduction of α,β-unsaturated carbonyl compounds, for selected examples, see:
About the conjugate reductions of β-heteroatom-substituted α,β-unsaturated esters, for two examples, see: