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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); Lu, CD
2017
Source PublicationJOURNAL OF ORGANIC CHEMISTRY
Volume82Issue:6Pages:3252-3261
AbstractEfficient 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.
DOI10.1021/acs.joc.6b03009
Indexed BySCI
WOS IDWOS:000397077500044
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Document Type期刊论文
Identifierhttp://ir.xjipc.cas.cn/handle/365002/4778
Collection省部共建新疆特有药用资源利用重点实验室
Corresponding AuthorLu, CD
Affiliation1.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
Recommended Citation
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 ,&Lu, CD.(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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