4.8 Article

Iron-Mediated Intramolecular Metalative Cyclization of α,β-Unsaturated Esters and Amides. Versatile One-Pot Preparation of Bicyclic Ketoesters

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ORGANIC LETTERS
卷 10, 期 21, 页码 5031-5033

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AMER CHEMICAL SOC
DOI: 10.1021/ol802170z

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  1. Ministry of Education, Culture. Sports, Science and Technology, Japan [16073208, 20750071]
  2. Grants-in-Aid for Scientific Research [16073208, 20750071] Funding Source: KAKEN

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2-Nonen-7-ynedioic or 2-decen-8-ynedioic acid derivatives were treated with an iron reagent generated from Fell and t-BuMgCl in a ratio of 1:4 to give cyclized products after hydrolysis, deuteriolysis, or the addition of carbonyl compounds. Upon reaction with the same iron reagent, 2,7-nonadienedioates afforded bicyclic ketoesters (and their enol forms) after the addition of s-BuOH or carbonyl compounds.

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