Samarium Diiodide Mediated Highly Diastereoselective Conjugate Reduction of the α,β-Unsaturated Ester Moiety in Heterocyclic Compounds

Hui Jiang; Risong Na; Lei Zhang; Honglei Liu; Zhen Li; Bo Wang; Hongchao Guo

doi:10.1055/s-0032-1317509

Synthesis, Table of Contents

Synthesis 2012; 44(23): 3633-3638
DOI: 10.1055/s-0032-1317509

paper

Samarium Diiodide Mediated Highly Diastereoselective Conjugate Reduction of the α,β-Unsaturated Ester Moiety in Heterocyclic Compounds

Hui Jiang

Department of Applied Chemistry, China Agricultural University, Beijing 100193, P. R. of China Fax: +86(10)62820325 Email: hchguo@cau.edu.cn

,

Risong Na

Department of Applied Chemistry, China Agricultural University, Beijing 100193, P. R. of China Fax: +86(10)62820325 Email: hchguo@cau.edu.cn

,

Lei Zhang

Department of Applied Chemistry, China Agricultural University, Beijing 100193, P. R. of China Fax: +86(10)62820325 Email: hchguo@cau.edu.cn

,

Honglei Liu

Department of Applied Chemistry, China Agricultural University, Beijing 100193, P. R. of China Fax: +86(10)62820325 Email: hchguo@cau.edu.cn

,

Zhen Li

Department of Applied Chemistry, China Agricultural University, Beijing 100193, P. R. of China Fax: +86(10)62820325 Email: hchguo@cau.edu.cn

,

Bo Wang

Department of Applied Chemistry, China Agricultural University, Beijing 100193, P. R. of China Fax: +86(10)62820325 Email: hchguo@cau.edu.cn

,

Hongchao Guo*

Department of Applied Chemistry, China Agricultural University, Beijing 100193, P. R. of China Fax: +86(10)62820325 Email: hchguo@cau.edu.cn

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Abstract

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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.

Key words

samarium diiodide - reduction - α,β-unsaturated ester - conjugate - heterocycle

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References

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