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

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posted on 2008-11-06, 00:00 authored by Takeshi Hata, Naoki Hirone, Shiro Sujaku, Kirihiro Nakano, Hirokazu Urabe
2-Nonen-7-ynedioic or 2-decen-8-ynedioic acid derivatives were treated with an iron reagent generated from FeCl2 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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