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Mo−Au Combo Catalysis for Rapid 1,3-Rearrangement of Propargyl Alcohols into α,β-Unsaturated Carbonyl Compounds
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Abstract
The combination of Mo and cationic Au catalysts dramatically accelerated the rearrangement of diverse propargyl alcohols, which includes a short reaction time, mild conditions, and high product yields. A practical application to the highly challenging primary propargyl alcohols and the N-alkynyl amides is achieved.
Citing Articles
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This article has been cited by 12 ACS Journal articles (5 most recent appear below).
Catalytic Asymmetric Synthesis of (+)-Anthecotulide Using Enyne and Meyer–Schuster Rearrangements
David M. Hodgson, Eric P. A. Talbot, and Barry P. ClarkOrganic Letters2011 13 (21), 5751-5753Catalytic Asymmetric Synthesis of (+)-Anthecotulide Using Enyne and Meyer–Schuster Rearrangements
David M. Hodgson, Eric P. A. Talbot, and Barry P. ClarkOrganic Letters2011 13 (21), 5751-5753The bioactive sesquiterpene lactone (+)-anthecotulide (1) is synthesized for the first time, in a six-step sequence devoid of protecting groups. The key transformations are a novel Rh(I)-catalyzed asymmetric enyne rearrangement of a terminal alkynyl ester ...
Contemporaneous Dual Catalysis: Chemoselective Coupling of Catalytic Vanadium-allenoate and π-Allylpalladium Intermediates
Barry M. Trost , Xinjun Luan , and Yan MillerJournal of the American Chemical Society 0 (ja),Contemporaneous Dual Catalysis: Chemoselective Coupling of Catalytic Vanadium-allenoate and π-Allylpalladium Intermediates
Barry M. Trost , Xinjun Luan , and Yan MillerJournal of the American Chemical Society 0 (ja),This paper presents a detailed investigation of a dual catalytic system that combines a vanadium-catalyzed Meyer-Schuster rearrangement and a palladium-catalyzed allylic alkylation. The implementation of this novel reaction relies on matching the ...
Gold-Catalyzed Carbon−Heteroatom Bond-Forming Reactions
A. Corma, A. Leyva-Pérez, and Maria J. SabaterChemical Reviews2011 111 (3), 1657-1712Gold-Catalyzed Carbon−Heteroatom Bond-Forming Reactions
A. Corma, A. Leyva-Pérez, and Maria J. SabaterChemical Reviews2011 111 (3), 1657-1712
A General Procedure for the Synthesis of Enones via Gold-Catalyzed Meyer−Schuster Rearrangement of Propargylic Alcohols at Room Temperature
Matthew N. Pennell, Matthew G. Unthank, Peter Turner, and Tom D. SheppardThe Journal of Organic Chemistry2011 76 (5), 1479-1482A General Procedure for the Synthesis of Enones via Gold-Catalyzed Meyer−Schuster Rearrangement of Propargylic Alcohols at Room Temperature
Matthew N. Pennell, Matthew G. Unthank, Peter Turner, and Tom D. SheppardThe Journal of Organic Chemistry2011 76 (5), 1479-1482Meyer−Schuster rearrangements of propargylic alcohols take place readily at room temperature in toluene with 1−2 mol % PPh3AuNTf2, in the presence of 0.2 equiv of 4-methoxyphenylboronic acid or 1 equiv of methanol. Good to excellent yields of enones can ...
Olefination of α,α′-Divinyl Ketones through Catalytic Meyer−Schuster Rearrangement
Curtis J. Rieder, Karl J. Winberg, and F. G. WestThe Journal of Organic Chemistry2011 76 (1), 50-56Olefination of α,α′-Divinyl Ketones through Catalytic Meyer−Schuster Rearrangement
Curtis J. Rieder, Karl J. Winberg, and F. G. WestThe Journal of Organic Chemistry2011 76 (1), 50-56The direct olefination of 1,4-dien-3-ones remains a synthetic challenge. A two-step protocol, employing acetylide addition followed by catalytic Meyer−Schuster rearrangement has been developed for the olefination of 1,4-pentadien-3-ones to afford [3]...
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History
- Published In Issue May 01, 2008
- Article ASAPApril 08, 2008
- Received: March 14, 2008
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