Gold-catalyzed cycloisomerization reactions of boronated enynes

Lee, Jack Chang Hung; Hall, Dennis G.

doi:10.1016/j.tetlet.2010.11.051

Cited by 19 publications

(7 citation statements)

References 41 publications

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“…It was previously shown that boronated enynes can be engaged successfully in various metal‐catalysed cycloisomerisation reactions allowing the construction of a range of stereodefined skeletally diverse molecules 12,18–20. The introduction of a pinacol boronic ester group in place of the ester function of enyne 1a was obtained via the synthesis of enyne 10 18a.…”

Section: Methodsmentioning

confidence: 99%

Antibacterial Agents and Cystic Fibrosis: Synthesis and Antimicrobial Evaluation of a Series of N‐Thiomethylazetidinones

et al. 2011

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The increasing emergence of multidrug-resistant microorganisms is one of the greatest challenges in the clinical management of infectious disease. New antimicrobial agents are therefore urgently required, particularly in the treatment of chronic and recurrent infections often associated with antibiotic-resistant pathogens, as in the case of cystic fibrosis (CF) patients. This study reports the antibacterial activity of a series of monocyclic β-lactams with an alkylidenecarboxyl chain or electron-withdrawing groups such as 4-OAc, 4-SAc, and 4-SO(2)Ph at the C4 position of the ring. N-Unsubstituted and N-thiomethyl derivatives were compared. A total of 33 azetidinones were tested for their activity against Gram-positive and Gram-negative bacterial clinical isolates. The combination of an N-thiomethyl group and a benzyl ester on the 4-alkylidene side chain were found to increase the potency against Gram-positive bacteria. The N-thiomethyl group clearly elevated the activity of 4-acetoxyazetidinones relative to the corresponding NH derivatives. The most active compounds showed minimum inhibitory concentration (MIC) values of 4 and 8 mg L(-1) against methicillin-resistant Staphylococcus aureus isolated from pediatric patients with CF.

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Section: Methodsmentioning

confidence: 99%

Antibacterial Agents and Cystic Fibrosis: Synthesis and Antimicrobial Evaluation of a Series of N‐Thiomethylazetidinones

et al. 2011

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“…161a 1,6-Enynes boronated at either the alkyne or the alkene react in a similar vein with Ph 3 PAuCl and AgSbF 6 . 176 …”

Section: Gold(i)-catalyzed Reactions Of Alkenes With Alkynesmentioning

confidence: 99%

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

2015

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“…The authors evaluated the effect of a boryl substituent on the cyclization of a prototypical 1,6-enyne cycloisomerization (Scheme 243, part A). 418 It was shown that the electronic effect of a pinacolboryl group located at the alkyne terminus of enyne 1034 did not alter the product selectivity obtained with the analogous substrate lacking the boryl substituent. 419 Only product 1035 resulting from a 5-exo-dig cyclization/endocyclic skeletal rearrangement pathway was obtained.…”

Section: Alkynylmentioning

confidence: 99%

“…The first study on the reactivity of alkynyl boronates under electrophilic gold catalysis was reported by Hall and coworkers in 2011. The authors evaluated the effect of a boryl substituent on the cyclization of a prototypical 1,6-enyne cycloisomerization (Scheme , part A) …”

Section: Carbon π-Systems With Electron-withdrawing Groupsmentioning

confidence: 99%

Gold-Catalyzed Reactions of Specially Activated Alkynes, Allenes, and Alkenes

et al. 2020

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This review describes the gold-catalyzed reactions of specially activated alkynes, allenes, and alkenes. Such species are characterized by the presence of either electron-donating or electron-withdrawing groups as substituents of the carbon π-system. They are intrinsically polarized, and when compared to their nonspecially activated counterparts can therefore be involved in gold-catalyzed transformations featuring increased regio-, stereo-, and chemoselectivities. The chemistry of specially activated carbon π-systems under homogeneous gold catalysis is extremely rich and varied. The reactivity observed with nonspecially activated unsaturated systems can often be transposed to specially activated ones without loss of efficiency. However, specially activated carbon π-systems also exhibit specific reactivities that cannot be attained with regular substrates. In this family of carbon π-systems, ynamides and their analogs, along with alkynyl carbonyl derivatives, are the classes of substrates that have retained the most attention. This review provides an overview of the chemistry developed with all classes of specially activated carbon π-systems by discussing their general and specific reactivities, presenting and commenting on their gold-catalyzed transformations as well as their applications.

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Gold-catalyzed cycloisomerization reactions of boronated enynes

Cited by 19 publications

References 41 publications

Antibacterial Agents and Cystic Fibrosis: Synthesis and Antimicrobial Evaluation of a Series of N‐Thiomethylazetidinones

Antibacterial Agents and Cystic Fibrosis: Synthesis and Antimicrobial Evaluation of a Series of N‐Thiomethylazetidinones

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

Gold-Catalyzed Reactions of Specially Activated Alkynes, Allenes, and Alkenes

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