Dialkyl Phosphite-Initiated Cyclopropanation of alpha,beta-Unsaturated Ketones Using alpha-Ketoesters or Isatin Derivatives | |
Yin, D (Yin, Deng); Liu, H (Liu, Hui); Lu, CD (Lu, Chong-Dao); Xu, YJ (Xu, Yan-Jun) | |
刊名 | JOURNAL OF ORGANIC CHEMISTRY
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2017 | |
卷号 | 82期号:6页码:3252-3261 |
通讯作者 | Lu, CD |
英文摘要 | Efficient cyclopropanation of alpha,beta-unsaturated ketones using alpha-ketoesters or isatin derivatives is reported. The cyclopropanation reaction occurs via a cascade transformation that starts with addition of deprotonated dialkyl phosphite to the keto groups of alpha-ketoesters or isatin derivatives, followed by [1,2]-phosphonate/phosphate rearrangement to generate alpha-phosphonyloxyenolate intermediates, which are trapped by alpha,beta-unsaturated ketones via Michael addition/ring closure. This protocol was used to synthesize tetra-substituted cyclopropanes with a 1,2-cis-1,3-trans configuration in high yield with excellent diastereos electivity. |
收录类别 | SCI |
WOS记录号 | WOS:000397077500044 |
内容类型 | 期刊论文 |
源URL | [http://ir.xjipc.cas.cn/handle/365002/4778] ![]() |
专题 | 新疆理化技术研究所_省部共建新疆特有药用资源利用重点实验室 |
作者单位 | 1.Chinese Acad Sci, Xinjiang Tech Inst Phys Chem, Key Lab Plant Resources & Chem Arid Zones, Urumqi 830011, Peoples R China 2.Univ Chinese Acad Sci, Beijing 100049, Peoples R China |
推荐引用方式 GB/T 7714 | Yin, D ,Liu, H ,Lu, CD ,et al. Dialkyl Phosphite-Initiated Cyclopropanation of alpha,beta-Unsaturated Ketones Using alpha-Ketoesters or Isatin Derivatives[J]. JOURNAL OF ORGANIC CHEMISTRY,2017,82(6):3252-3261. |
APA | Yin, D ,Liu, H ,Lu, CD ,&Xu, YJ .(2017).Dialkyl Phosphite-Initiated Cyclopropanation of alpha,beta-Unsaturated Ketones Using alpha-Ketoesters or Isatin Derivatives.JOURNAL OF ORGANIC CHEMISTRY,82(6),3252-3261. |
MLA | Yin, D ,et al."Dialkyl Phosphite-Initiated Cyclopropanation of alpha,beta-Unsaturated Ketones Using alpha-Ketoesters or Isatin Derivatives".JOURNAL OF ORGANIC CHEMISTRY 82.6(2017):3252-3261. |
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