A new approach to 3-hydroxyprolinol derivatives by samarium diiodide-mediated reductive coupling of chiral nitrone with carbonyl compounds.
A new approach to 3-hydroxyprolinol derivatives by samarium diiodide-mediated reductive coupling of chiral nitrone with carbonyl compounds.
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DOI：
10.1039/b906224f
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发表时间：
2009-07
影响因子：
3.2
通讯作者：
Shao-feng Wu;Xiao Zheng;Yuanping Ruan;Pei‐Qiang Huang
中科院分区：
文献类型：
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作者：
Shao-feng Wu;Xiao Zheng;Yuanping Ruan;Pei‐Qiang Huang
描述了一种灵活的反式-(3S)-羟基脯氨醇衍生物的非对映选择性方法，该方法基于二碘化钐介导的手性1-吡咯啉N-氧化物(硝酮)(S)-10与羰基化合物的还原偶联。硝酮 10 与酮和芳香醛的还原羟烷基化在建立吡咯烷环的 C-2 手性中心方面具有高度非对映选择性。
A flexible diastereoselective approach to trans-(3S)-hydroxyprolinol derivatives is described, which is based on the samarium diiodide-mediated reductive coupling of the chiral 1-pyrroline N-oxide (nitrone)(S)-10 with carbonyl compounds. The reductive hydroxyalkylation of nitrone 10 with ketones and aromatic aldehydes is highly diastereoselective in establishing the C-2 chiral center of the pyrrolidine ring.