Enantioselective Friedel–Crafts Alkylation Reactions of β‐Naphthols with Donor–Acceptor Aminocyclopropanes

Zhu, Man; Wang, Dongchao; Xie, Ming‐Sheng; Qu, Gui‐Rong; Guo, Hai‐Ming

doi:10.1002/chem.201804032

Cited by 30 publications

(11 citation statements)

References 88 publications

(24 reference statements)

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“…D–A aminocyclopropanes have also been used by Guo and co-workers in the copper-catalyzed asymmetric Friedel–Crafts alkylation of β-naphthols using bisoxazoline ligand 112 (Scheme ). In contrast to the alkylation of naphthols with aryl-substituted cyclopropanes reported by Feng and co-workers, both C - and O -alkylations were observed with aminocyclopropanes with a chemoselectivity in favor of the C -alkylation. A range of γ-aryl GABA derivatives such as 113 – 116 was produced in good yields and high ee.…”

Section: Donor–acceptor Cyclopropanescontrasting

confidence: 87%

Catalytic Enantioselective Ring-Opening Reactions of Cyclopropanes

2020

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This review describes the development of enantioselective methods for the ring opening of cyclopropanes. Both approaches based on the reaction of nonchiral cyclopropanes and (dynamic) kinetic resolutions and asymmetric transformations of chiral substrates are presented. The review is organized according to substrate classes, starting by the more mature field of donor−acceptor cyclopropanes. Emerging methods for enantioselective ring opening of acceptor-or donor-only cyclopropanes are then presented. The last part of the review describes the ring opening of more reactive three-membered rings substituted with unsaturations with a particular focus on vinylcyclopropanes, alkylidenecyclopropanes, and vinylidenecyclopropanes. In the last two decades, the field has grown from a proof of concept stage to a broad range of methods for accessing enantioenriched building blocks, and further extensive developments can be expected in the future.

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Section: Donor–acceptor Cyclopropanescontrasting

confidence: 87%

Catalytic Enantioselective Ring-Opening Reactions of Cyclopropanes

2020

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“…Enantioselective Friedel–Crafts alkylations of β-naphthols with DA aminocyclopropanes were reported later by the Guo group (Scheme B) . The reaction leads to the formation of a series of γ-aryl γ-aminobutyric acid derivatives 82 with high enantioselectivity and yields using Cu(OTf) 2 and bisoxazoline ligand L .…”

Section: Methodologies Employing Donor–acceptor Cyclopropylamine Deri...mentioning

confidence: 94%

Selective Carbon–Carbon Bond Cleavage of Cyclopropylamine Derivatives

2020

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This review summarizes synthetic developments reported from 1987 to 2019 that exploit C–C single bond cleavage of cyclopropylamine-based systems. The synthetic and mechanistic aspects of key methodologies are highlighted, and examples where aminocyclopropanes are exploited as key intermediates in multistep synthesis are also discussed. The review encompasses cases where aminocyclopropanes participate in polar reactions, pericyclic processes, radical-based reactions, and C–C bond activations.

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“…By using the Cu II / L4 catalyst, products of C‐nucleophilic ring‐opening were isolated in excellent yield and enantioselectivity, accompanying by products of O‐nucleophilic ring‐opening (Scheme 6 b). This catalytic system also performed well with 1,3,5‐trimethoxybenzene and N ‐methylindole nucleophiles [14] …”

Section: Asymmetric Reactions Of 2‐substituted Cyclopropane‐11‐dicarboxylatesmentioning

confidence: 87%

Asymmetric Catalytic Reactions of Donor–Acceptor Cyclopropanes

2020

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Due to the synergistic “push–pull” effect of vicinal electron‐donating and electron‐withdrawing groups, donor–acceptor (D‐A) cyclopropanes have been recognized as one of the most powerful building blocks to generate polyfunctional reactive intermediates after a strain‐driven ring cleavage. Enantioselective reactions of D‐A cyclopropanes provide an efficient approach to enantioenriched acyclic and cyclic compounds. A number of chiral Lewis/Brønsted acids, transition metals, and organocatalysts have been designed for such transformations, including ring‐openings, annulations, and rearrangements. This minireview highlights the developments and new advances in this field and describes new synthetic opportunities offered by these interesting methodologies.

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Enantioselective Friedel–Crafts Alkylation Reactions of β‐Naphthols with Donor–Acceptor Aminocyclopropanes

Cited by 30 publications

References 88 publications

Catalytic Enantioselective Ring-Opening Reactions of Cyclopropanes

Catalytic Enantioselective Ring-Opening Reactions of Cyclopropanes

Selective Carbon–Carbon Bond Cleavage of Cyclopropylamine Derivatives

Asymmetric Catalytic Reactions of Donor–Acceptor Cyclopropanes

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