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学科主题: 有机化学
题名: Development of a new reaction system for the synthesis of highly optically active α,γ-substituted γbutyrolactones
其他题名: 高立体选择性地合成光学活性的α,γ-取代γ-丁内酯
作者: Xu MH(徐明华) ; Wang W(王伟) ; Xia LJ(夏立钧) ; Lin GQ(林国强)
通讯作者: 林国强
刊名: J. Org. Chem.
发表日期: 2001-01-01
卷: 66, 期:11, 页:3953-3962
收录类别: SCI
部门归属: 中国科学院上海有机化学研究所现代有机化学实验室
英文摘要: A highly useful method for the synthesis of optically active α,γ-substituted γ-butyrolactones has been developed. The SmI^2-induced reductive coupling of chiral 2-alkyl acrylates deriv ed from isosorbide with ketones in the presence of (1S)-(-)-2,10-camphorsultam as a proton source give the chiral α,γ-substituted γ-butyrolactones in good yields and high enantiomeric purities (up to >99% ee for trans and 75% ee for cis). The reaction system has been investigated with various ketones, and it is demonstrated that this system is very effective for trans- α,γ-substituted --butyrolactones. Oth the chiral auxiliary and the hindered proton source in this system are necessary for the observed excellent ee values of the products. The absolute configuration of the trans products is assigned on the basis of the X-ray crystal structure.
语种: 英语
相关网址: 查看原文
内容类型: 期刊论文
URI标识: http://ir.sioc.ac.cn/handle/331003/16575
Appears in Collections:中科院天然产物有机化学重点实验室_期刊论文

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Recommended Citation:
Xu MH,Wang W,Xia LJ,et al. Development of a new reaction system for the synthesis of highly optically active α,γ-substituted γbutyrolactones[J]. J. Org. Chem.,2001,66(11):3953-3962.
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