Journal Article10.1021/JA037655V
Catalyzed Olefin Isomerization Leading to Highly Stereoselective Claisen Rearrangements of Aliphatic Allyl Vinyl Ethers
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TL;DR: Iridium(I)-catalyzed olefin isomerization in bis(allyl) ethers is integrated into a generally applicable strategy for affecting highly stereoselective Claisen rearrangements.
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Abstract: Iridium(I)-catalyzed olefin isomerization in bis(allyl) ethers is integrated into a generally applicable strategy for affecting highly stereoselective Claisen rearrangements. Catalyzed alkene isomerization affords allyl vinyl ethers from easily prepared di(allyl) ethers; direct thermolysis of these reaction mixtures leads to highly diastereoselective [3,3] sigmatropic rearrangements affording syn-2,3-dialkyl-4-pentenal derivatives. An easily executed strategy for realizing asymmetric variants of the isomerization-Claisen rearrangement (ICR) reactions is also described.
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Citations
A temporary stereocentre approach for the asymmetric synthesis of chiral cyclopropane-carboxaldehydes.
TL;DR: The potential of this methodology has been demonstrated for the asymmetric synthesis of the cyclopropane containing natural product cascarillic acid in good yield.
Base-Mediated Cascade Rearrangements of Aryl-Substituted Diallyl Ethers
Jolene P. Reid,Catherine A. McAdam,Adam J. S. Johnston,Matthew N. Grayson,Jonathan M. Goodman,Matthew J. Cook +5 more
TL;DR: Two base-mediated cascade rearrangement reactions of diallyl ethers were developed leading to selective [2,3]-Wittig-oxy-Cope and isomerization-Claisen rearrangements, demonstrating that the role of the base and solvent was key to the reactivity and selectivity observed.
Nickel-Catalyzed Double Bond Transposition of Alkenyl Boronates for in Situ syn-Selective Allylboration Reactions.
TL;DR: The transposition of a homoallyl pinacol boronic ester was realized by a highly reactive nickel-catalyst system comprising NiCl2(dppp), zinc powder, ZnI2, and Ph2PH in high diastereoselectivities.
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Homologation of monoterpenoids into new sesquiterpenoids via tandem isomerisation/claisen rearrangement reactions with three-component ruthenium catalysts, and Ru(methallyl)2 (COD) revealed by high throughput screening techniques
TL;DR: In this article, a catalytic system based on a ruthenium source Ru 3 (CO) 1 2, a bulky imidazolinium salt and Cs 2 CO 3 appears very efficient for the transformation of a 1,7-diene into a γ,δ-unsaturated aldehyde via tandem isomerisation/Claisen reactions.
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References
Asymmetric Claisen rearrangement
Hisanaka Ito,Takeo Taguchi +1 more
TL;DR: In this review article, recent advances in the asymmetric Claisen rearrangement are described.
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Chloro- and bromo-(alkene)iridium(I) complexes☆
TL;DR: In this article, it was shown that the metal-alkene and metal-chlorine bonds are stronger in the iridium(I) compounds than in the chloro compounds.
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