Regioselective Cyclizations Utilizing a Gold‐Catalyzed [3,3] Propargyl Ester Rearrangement

Cran, John W.; Krafft, Marie E.

doi:10.1002/ange.201203923

Cited by 10 publications

(2 citation statements)

References 62 publications

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“…1, n -Enynes 392 with a conjugated enone react by a different mechanism involving a 1,3-acyloxy migration to form acyloxyallenes 393 , which undergo a Michael addition to form cyclic products 394 (Scheme 124 ). 331 …”

Section: Gold(i)-catalyzed Reactions Of Propargylic Carboxylatesmentioning

confidence: 99%

Gold(I)-Catalyzed Activation of Alkynes for the Construction of Molecular Complexity

2015

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Section: Gold(i)-catalyzed Reactions Of Propargylic Carboxylatesmentioning

confidence: 99%

Gold(I)-Catalyzed Activation of Alkynes for the Construction of Molecular Complexity

2015

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“…To prove our hypothesis, we chose 3a as the model substrate. [15] To our delight, the desired product 4a was obtained (99 %y ield) in an open flask catalyzedb yt riflic acid (2.5 mol %) with wet nitromethane as the solvent. Fortunately,o ur method is applicable to synthesize as eries of symmetrical and unsymmetricalu nsaturated carbocycles.…”

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confidence: 99%

Triflic Acid‐Catalyzed Enynes Cyclization: A New Strategy beyond Electrophilic π‐Activation

Liu

Zhang

2016

Chemistry A European J

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The cyclization of enynes, catalyzed by a transition metal, represents a powerful tool to construct an array of cyclic compounds through electrophilic π-activation. In this paper, we disclose a new and efficient strategy for enynes cyclization catalyzed by triflic acid. The salient features of this transformation includes a broad substrate scope, metal free synthesis, open flask and mild conditions, good yields, ease of operation, low catalyst loading, and easy scale-up to gram scale. A preliminary mechanism study demonstrated that the activation model of the reaction was σ-activation, which is different from the transition-metal-catalyzed enynes cyclization. Our strategy affords a complementary method to the traditional strategies, which use transition-metal catalysts.

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Design and Synthesis of Alanine Triazole Ligands and Application in Promotion of Hydration, Allene Synthesis and Borrowing Hydrogen Reactions

et al. 2016

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An ew type of alanine triazole( ATA) ligand was found to be an efficientp artner for the stabilizationo fg old(III), thus rendering improved stability andh igh catalytic activities in allene synthesis and hydration reactions through the 3,3'-arrangement of propargyl estersa nd propargyl alcohols.I na ddition to Au(I), ATA-gold(III) was also proven to be an effective catalyst in promoting the formation of allenes with high yields.F urthermore, alanine triazoler uthenium hase xhibited excellent potentiala sameans to catalyze borrowingh ydrogen of alcohols andamines,ketones and alcohols.

show abstract

Regioselective Cyclizations Utilizing a Gold‐Catalyzed [3,3] Propargyl Ester Rearrangement

Cited by 10 publications

References 62 publications

Gold(I)-Catalyzed Activation of Alkynes for the Construction of Molecular Complexity

Gold(I)-Catalyzed Activation of Alkynes for the Construction of Molecular Complexity

Triflic Acid‐Catalyzed Enynes Cyclization: A New Strategy beyond Electrophilic π‐Activation

Design and Synthesis of Alanine Triazole Ligands and Application in Promotion of Hydration, Allene Synthesis and Borrowing Hydrogen Reactions

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