Iron-catalyzed allylic amination

Johannsen, Mogens; Joergensen, Karl Anker

doi:10.1021/jo00080a034

Cited by 71 publications

(40 citation statements)

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“…Compound 3 a is commercially available and its analytical data were compared with those of an authentic sample. Analytical data for compounds 3 b, [14] 3 d, [15] 3 e, [16] and 3 h [17] were in complete accordance with literature values. 10 mmol).…”

Section: Methodssupporting

confidence: 86%

Zirconium‐Mediated Coupling Reactions of Amines and Enol or Allyl Ethers: Synthesis of Allyl‐ and Homoallylamines

Barluenga

Rodríguez

Alvarez‐Rodrigo

et al. 2003

Chemistry A European J

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An easy and efficient zirconium-mediated synthesis of allylamines from simple amines and enol ethers is described. This strategy also allows the synthesis of amino alcohol derivatives containing a Z double bond in their structure when 2,3-dihydrofuran is used. Simple conventional modification of these amino alcohols leads to 2-substituted piperidine derivatives. By applying this approach, a formal total synthesis of the alkaloid coniine is easily achieved from a protected butylamine. Finally, the zirconium-mediated reaction of amines and allyl phenyl ether furnishes homoallylamines or amino ethers depending on the structure of the starting amine.

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Section: Methodssupporting

confidence: 86%

Zirconium‐Mediated Coupling Reactions of Amines and Enol or Allyl Ethers: Synthesis of Allyl‐ and Homoallylamines

Barluenga

Rodríguez

Alvarez‐Rodrigo

et al. 2003

Chemistry A European J

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“…An iron(II)À phthalocyanine-catalyzed allylic amination with phenylhydroxylamine had already been reported by Jørgensen and Johannsen in 1994. 629 Later in the same year, Nicholas and Srivastava described the same transformation using various iron(II) and iron(III) salts as catalysts. 630 Benzylic CÀH bonds have been used for oxidative coupling reactions with benzamides and benzenesulfonamides in the presence of iron(II) chloride as catalyst and N-bromosuccinimide (NBS) as oxidant (Scheme 344).…”

Section: Scheme 332mentioning

confidence: 98%

Iron Catalysis in Organic Synthesis

2015

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“…31 Recently, a hetero-bimetallic Pd and Cr catalytic protocol has also been developed to affect a similar amination reaction. 27 We have proposed two possible mechanistic pathways (Fig.…”

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confidence: 99%