The Preparation and Rearrangement of Allyl Kojate

McLamore, W. M.; Gelblum, Ernestine; Bavley, A.

doi:10.1021/ja01593a046

Cited by 13 publications

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“…75 This study was repeated in 1956 by McLamore, Gelblum and Bavley) and the original results were contested (Scheme 44; see also Scheme 37). 76 According Decades later, the rate-enhancing effect of hydrogenbond-donor solvents was studied in a seminal work by Severance and Jorgensen. 25 They employed a QM/MM approach at the OPLS/TIP4P level of theory.…”

Section: Claisen Rearrangement Using Stable Enols: Kojic Acid and Diomentioning

confidence: 99%

Claisen Rearrangement of Aliphatic Allyl Vinyl Ethers from 1912 to 2012: 100 Years of Electrophilic Catalysis

Rehbein

Hiersemann

2013

Synthesis

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This review summarizes, from a personal perspective, the development of catalytic asymmetric Claisen rearrangements from 1912 to 2012. 1 Introduction 2 Gosteli-Claisen Rearrangement 3 Claisen Rearrangement Using Stable Enols: Kojic Acid and Diosphenols 4 The Early Years: Catalysis by Brønsted Acids 5 Lewis Acid Mediated Claisen Rearrangements: The Aluminum Age 6 Catalysis by Precious Metals 7 Catalysis by σ-Lewis Acids 8 Catalysis by Achiral Organocatalysts 9 Catalytic Asymmetric Claisen Rearrangements 10 Conclusion

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Section: Claisen Rearrangement Using Stable Enols: Kojic Acid and Diomentioning

confidence: 99%

Claisen Rearrangement of Aliphatic Allyl Vinyl Ethers from 1912 to 2012: 100 Years of Electrophilic Catalysis

Rehbein

Hiersemann

2013

Synthesis

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“…The Claisen rearrangement of allylic ethers of the pyrone natural product kojic acid 1 has provided access to interesting bioactive compounds. Such reactions are key to the preparation of early intermediates in syntheses of phorbol and related compounds, 2 and our lab has used the aromatic version of this process to access heterocyclic biaryls.…”

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“…Catalysts for the rearrangement of 2 were screened at 10 mol% under a standard set of conditions: 0.028 M in toluene, microwave heating at 100 °C, 1 h. It is simple to determine reaction progress by 1 H NMR spectroscopy using the integration of the vinylic hydrogens in the crude reaction product. These reactions are clean and in all cases the product was isolated in pure form.…”

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Catalyzed Claisen rearrangements of O-allyl kojates

Pirrung

Nalbandian

2013

Tetrahedron Letters

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TheClaisen andCope Rearrangements

Rhoads

Raulins

2011

Organic Reactions

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Since the first observation of a thermal rearrangement vinyl allyl ether to the corresponding homoallylcyclic carbonyl compound by Claisen in 1912, rearrangements of vinyl and aryl allylic ethers have been extensively studied and exploited for their synthetic value. The corresponding rearrangement of substituted 1,5‐hexadiene was first recognized by Cope in 1940 as the carbon analog of the Claisen rearrangement. Today it is recognized that such transformations fall within the general category of a [3,3] sigamtropic reaction and that considerable variation may be accommodated in the basic requirement of a system of six atoms with terminal unsaturated linkage. This chapter attempts to survey the vas t accumulation of Claisen and Cope rearrangements recorded since the first coverage in 1944.

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The Preparation and Rearrangement of Allyl Kojate

Cited by 13 publications

References 0 publications

Claisen Rearrangement of Aliphatic Allyl Vinyl Ethers from 1912 to 2012: 100 Years of Electrophilic Catalysis

Claisen Rearrangement of Aliphatic Allyl Vinyl Ethers from 1912 to 2012: 100 Years of Electrophilic Catalysis

Catalyzed Claisen rearrangements of O-allyl kojates

TheClaisen andCope Rearrangements

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