Switchable Reactions of Cyclopropanes with Enol Silyl Ethers. Controllable Synthesis of Cyclopentanes and 1,6-Dicarbonyl Compounds | |
Qu JP(曲剑萍) ; Deng C(邓超) ; Zhou J(周剑) ; Sun XL(孙秀丽) ; Tang Y(唐勇) | |
刊名 | J. Org. Chem. |
2009 | |
卷号 | 74期号:20页码:7684-7689 |
ISSN号 | 0022-3263 |
其他题名 | Switchable Reactions of Cyclopropanes with Enol Silyl Ethers. Controllable Synthesis of Cyclopentanes and 1,6-Dicarbonyl Compounds |
通讯作者 | 唐勇 |
英文摘要 | Cu(SbF6)(2)-catalyzed reaction of 2-substituted cyclopropane-1,1-dicarboxylates 1 with enol silyl ethers 2 call be readily controlled: the reaction undergoes a cycloaddition to provide substituted cyclopentane derivatives 3 in excellent yields with high diastereoselectivities in the presence of complex 8/Cu(II); however, the same substrates afford acyclic 1,6-dicarbonyl products 4 via a cycloaddition-ring-opening reaction in tip to 92% yield in the absence of ligand 8. The mechanism for the ligand-switchable reactions was investigated by both control experiments and H-1 NMR studies. The substrate scope and limitation of the tunable transformation were also examined. |
学科主题 | 有机化学 |
收录类别 | SCI |
原文出处 | http://dx.doi.org/10.1021/jo901340v |
语种 | 英语 |
WOS记录号 | WOS:000270504900011 |
公开日期 | 2013-02-25 |
内容类型 | 期刊论文 |
源URL | [http://202.127.28.38/handle/331003/19363] |
专题 | 上海有机化学研究所_金属有机化学国家重点实验室 |
推荐引用方式 GB/T 7714 | Qu JP,Deng C,Zhou J,et al. Switchable Reactions of Cyclopropanes with Enol Silyl Ethers. Controllable Synthesis of Cyclopentanes and 1,6-Dicarbonyl Compounds[J]. J. Org. Chem.,2009,74(20):7684-7689. |
APA | 曲剑萍,邓超,周剑,孙秀丽,&唐勇.(2009).Switchable Reactions of Cyclopropanes with Enol Silyl Ethers. Controllable Synthesis of Cyclopentanes and 1,6-Dicarbonyl Compounds.J. Org. Chem.,74(20),7684-7689. |
MLA | 曲剑萍,et al."Switchable Reactions of Cyclopropanes with Enol Silyl Ethers. Controllable Synthesis of Cyclopentanes and 1,6-Dicarbonyl Compounds".J. Org. Chem. 74.20(2009):7684-7689. |
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