Synthesis 2012; 44(23): 3633-3638
DOI: 10.1055/s-0032-1317509
paper
© Georg Thieme Verlag Stuttgart · New York

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
› Author Affiliations
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