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
Enantioselective Synthesis of anti Homoallylic Alcohols from Terminal Alkynes and Aldehydes Based on Concomitant Use of a Cationic Iridium Complex and a Chiral Phosphoric Acid.
TL;DR: In this article, a highly diastereo and enanti-lective synthesis of anti homoallylic alcohols from terminal alkynes via (E)-1-alkenylboronates based upon two catalytic reactions was reported.
45
Iridium-Catalyzed Allylation of Chiral β-Stereogenic Alcohols: Bypassing Discrete Formation of Epimerizable Aldehydes
TL;DR: The cyclometalated π-allyliridium 3,4-dinitro-C,O-benzoate complex modified by (R)- or (S)-Cl,MeO-BIPHEP promotes the transfer hydrogenative coupling of allyl acetate to β-stereogenic alcohols with good to excellent levels of catalyst-directed diastereoselectivity to furnish homoallylic alcohols.
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Metalloporphyrin Cr(TPP)Cl-catalyzed Claisen rearrangement of simple aliphatic allyl vinyl ethers and its unique stereoselectivity
TL;DR: In this paper, the authors used a chromium(III) porphyrin complex, Cr(TPP)Cl, as a catalyst for the thermal Claisen rearrangement of simple aliphatic allyl vinyl ethers.
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Asymmetric Synthesis of α-Substituted Aldehydes by Pd-Catalyzed Asymmetric Allylic Alkylation−Alkene Isomerization−Claisen Rearrangement
Barry M. Trost,Ting Zhang +1 more
TL;DR: An asymmetric synthesis of communiol A was accomplished applying the Pd-catalyzed asymmetric allylic alkylation methodology, with remarkable chemoselectivity in the olefin isomerization step.
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Alkynes to (E)-enolates using tandem catalysis: stereoselective anti-aldol and syn-[3,3]-rearrangement reactions
Neil P. Grimster,Donna Wilton,Louis K. M. Chan,Christopher Richard Ayles Godfrey,Clive Green,Dafydd R. Owen,Matthew J. Gaunt +6 more
TL;DR: A new tandem catalysis strategy that transforms alkyne derivatives to (E)-enol-equivalents followed by stereoselective anti-selective aldol coupling or syn- selective [3,3]-rearrangement transformations is reported.
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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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