Nickel(0)‐Catalyzed Enantioselective Annulations of Alkynes and Arylenoates Enabled by a Chiral NHC Ligand: Efficient Access to Cyclopentenones

Ahlin, Joachim S. E.; Donets, Pavel A.; Cramer, Nicolai

doi:10.1002/anie.201408364

Cited by 59 publications

(19 citation statements)

References 76 publications

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“…Cramer et al discloseahighly enantioselective Ni 0 -catalyzed reductive[ 3 + +2] cycloaddition of a,b-unsaturated aromatic mesityl enoates and internal alkynes for the asymmetric synthesis of cyclopentenones (Scheme 27). [64] Ligands, represented by chiral, bulky, C 1 -symmetric N-heterocyclic carbene L1 and non-C 2 -symmetric chiral carbene ligand L2,e nablet he transformation to occurat5 08Cb yemployingC PME as the solvent.…”

Section: Use Of Cpme In Transition-metal-catalyzed Chemistrymentioning

confidence: 99%

Cyclopentyl Methyl Ether: An Elective Ecofriendly Ethereal Solvent in Classical and Modern Organic Chemistry

et al. 2018

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Solvents represent one of the major contributions to the environmental impact of fine‐chemical synthesis. As a result, the use of environmentally friendly solvents in widely employed reactions is a challenge of vast real interest in contemporary organic chemistry. Within this Review, a great variety of examples showing how cyclopentyl methyl ether has been established as particularly useful for this purpose are reported. Indeed, its low toxicity, high boiling point, low melting point, hydrophobicity, chemical stability towards a wide range of conditions, exceptional stability towards the abstraction of hydrogen atoms, relatively low latent heat of vaporization, and the ease with which it can be recovered and recycled enable its successful employment as a solvent in a wide range of synthetic applications, including organometallic chemistry, catalysis, biphasic reactions, oxidations, and radical reactions.

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Section: Use Of Cpme In Transition-metal-catalyzed Chemistrymentioning

confidence: 99%

Cyclopentyl Methyl Ether: An Elective Ecofriendly Ethereal Solvent in Classical and Modern Organic Chemistry

et al. 2018

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“…On the other hand, another type of enantioselective nickel‐catalyzed annulation reaction occurring between α,β‐unsaturated aromatic esters 77a–q and alkynes 78a–f was reported by Cramer et al., leading to chiral cyclopentenones 79a–u 44. This formal [3+2] cycloaddition was promoted by a combination of Ni(cod) 2 and chiral bulky C 1 ‐symmetrical N ‐ heterocyclic carbene ligand 80 in the presence of superstoichiometric amounts of BEt 3 and tert‐ butyl alcohol in cyclopentyl methyl ether (CPME) as solvent.…”

Section: Enantioselective Metal‐catalyzed Mono‐ and Two‐component Dmentioning

confidence: 97%

Recent Developments in Enantioselective Metal‐Catalyzed Domino Reactions

Pellissier

2016

Adv Synth Catal

106

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International audienceThis review updates the major progress in the field of enantioselective one-, two-, and multicomponent domino reactions promoted by chiral metal catalysts, covering the literature since the beginning of 2012. It illustrates how enantioselective metal-catalyzed processes have emerged as outstanding tools for the development of a wide variety of fascinating one-pot asymmetric domino reactions, allowing complex and diverse structures to be easily generated from simple materials in a single step. During the last 4 years, a myriad of already existing as well as completely novel and powerful asymmetric domino processes have been developed on the basis of asymmetric metal catalysis, taking economical advantages, such as avoiding costly protecting groups and time-consuming purification procedures after each step

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“…Using Kündig's modification of this chiral carbene family (L2), the selectivity could be improved, but the conversion remained low (Entry 2). [3b,19] Replacing one of the chiral N-alkyl substituents with a bulky 2,6-diisopropyl phenyl group [20] as in L3 and L4, significantly improved the conversion of the reaction and the product was obtained in high yield, but with poor enantioselectivity (Entries 3 and 4). Hong's carbenes (e.g.…”

Section: Chiral N-heterocyclic Carbene Ligands For Asymmetric Transit...mentioning

confidence: 99%

Modular Chiral N-Heterocyclic Carbene Ligands for the Nickel-Catalyzed Enantioselective C–H Functionalization of Heterocycles

Diesel

Cramer

2020

Chimia

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N-Heterocyclic carbenes (NHCs) are the ligands of choice in a large variety of transformations entailing different transition metals. However, the number and variety of chiral NHCs suitable as stereo-controlling ligands in asymmetric catalysis remains limited. Herein we highlight the introduction of a modular NHC ligand family, consisting of a chiral version of the widely used IPr ligand. These chiral NHC ligands were applied in the nickel-catalyzed enantioselective C–H functionalization of N-heterocycles. Nickel-NHC catalysis unlocked the stereoselective C–H annulation of 2- and 4-pyridones, delivering fused bicyclic compounds found in many biologically active compounds. Applying a bulky, yet flexible ligand scaffold enabled the highly enantioselective C–H functionalization of pyridones under mild conditions. The introduction of a bulky chiral SIPr analogue enabled the nickel-catalyzed enantioselective C–H functionalization of indoles, yielding valuable tetrahydropyridoindoles. Additionally, pyrrolopyridines, pyrrolopyrimidines and pyrroles were efficiently functionalized, delivering chiral annulated azoles.

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Nickel(0)‐Catalyzed Enantioselective Annulations of Alkynes and Arylenoates Enabled by a Chiral NHC Ligand: Efficient Access to Cyclopentenones

Cited by 59 publications

References 76 publications

Cyclopentyl Methyl Ether: An Elective Ecofriendly Ethereal Solvent in Classical and Modern Organic Chemistry

Cyclopentyl Methyl Ether: An Elective Ecofriendly Ethereal Solvent in Classical and Modern Organic Chemistry

Recent Developments in Enantioselective Metal‐Catalyzed Domino Reactions

Modular Chiral N-Heterocyclic Carbene Ligands for the Nickel-Catalyzed Enantioselective C–H Functionalization of Heterocycles

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