6‐Azabicyclo[3.2.1]octanes <i>via</i> Copper‐Catalyzed Enantioselective Alkene Carboamination

Casavant, Barbara J.; Hosseini, Azade S.; Chemler, Sherry R.

doi:10.1002/adsc.201400317

Cited by 24 publications

(14 citation statements)

References 37 publications

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“…In the context of copper-catalyzed heterocycle synthesis, we have explored both doubly intramolecular 48–51 and intra-/intermolecular 52 carboamination approaches.…”

Section: Resultsmentioning

confidence: 99%

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Stereoselective and Regioselective Synthesis of Heterocycles via Copper-Catalyzed Additions of Amine Derivatives and Alcohols to Alkenes

2017

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This Perspective describes the development of a family of copper(II)-catalyzed alkene difunctionalization reactions that enable stereoselective addition of amine derivatives and alcohols onto pendant unactivated alkenes to provide a range of valuable saturated nitrogen and oxygen heterocycles. 2-Vinylanilines and related substrates undergo alternative oxidative amination or allylic amination pathways, and these reactions will also be discussed. The involvement of both polar and radical steps in the reaction mechanisms have been implicated. Major product formation is a function of the lowest energy pathway, which in turn is a function of structural aspects of the various reaction components.

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“…In the context of copper-catalyzed heterocycle synthesis, we have explored both doubly intramolecular 48–51 and intra-/intermolecular 52 carboamination approaches.…”

Section: Resultsmentioning

confidence: 99%

“…51 When N -alkylsulfonyl-2-aryl-4-pentenylamines are applied, enantioselective carboamination occurs smoothly to form variously substituted 6-azabicyclo[3.2.1]octanes (Scheme 11). 51 …”

Section: Resultsmentioning

confidence: 99%

Stereoselective and Regioselective Synthesis of Heterocycles via Copper-Catalyzed Additions of Amine Derivatives and Alcohols to Alkenes

2017

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“…If the alkene was 1,1 disubstituted the reaction proceeded smoothly but when 1,2-disubstituted the reaction halted completely, not giving any product. 237 …”

Section: Bis(oxazoline) Ligandsmentioning

confidence: 99%

Further Developments and Applications of Oxazoline-Containing Ligands in Asymmetric Catalysis

et al. 2021

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The chiral oxazoline motif is present in many ligands that have been extensively applied in a series of important metal-catalyzed enantioselective reactions. This Review aims to provide a comprehensive overview of the most significant applications of oxazoline-containing ligands reported in the literature starting from 2009 until the end of 2018. The ligands are classified not by the reaction to which their metal complexes have been applied but by the nature of the denticity, chirality, and donor atoms involved. As a result, the continued development of ligand architectural design from mono(oxazolines), to bis(oxazolines), to tris(oxazolines) and tetra(oxazolines) and variations thereof can be more easily monitored by the reader. In addition, the key transition states of selected asymmetric transformations will be given to illustrate the features that give rise to high levels of asymmetric induction. As a further aid to the reader, we summarize the majority of schemes with representative examples that highlight the variation in % yields and % ee s for carefully selected substrates. This Review should be of particular interest to the experts in the field but also serve as a useful starting point to new researchers in this area. It is hoped that this Review will stimulate both the development/design of new ligands and their applications in novel metal-catalyzed asymmetric transformations.

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“…On the other hand, the reactions of N-mesyl-4-pentenylamines having the geminal diaryl moiety at the C2 position under the Cu(OTf) 2 -(R,R)-Ph-Box catalytic system in the presence of MnO 2 provided 6-azabicyclo[3.2.1]octane in high enantioselectivity through carboamination of alkenes (Scheme 58-iii). 81 The transient C-radicals generated via aminocupration of N-sulfonyl alkenylamines could undergo an iodine transfer reaction with isopropyl iodide to form the corresponding 2-iodomethyl indolines and pyrrolidines (Scheme 59). 82 Similarly, chlorination and bromination reactions were achieved in moderate yields using 1,1-dichloroethylene and (2,2-dibromo-1-methylcyclopropyl)benzene.…”

Section: Mnomentioning

confidence: 99%

Copper-catalyzed oxidative carbon–heteroatom bond formation: a recent update

2016

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6‐Azabicyclo[3.2.1]octanes via Copper‐Catalyzed Enantioselective Alkene Carboamination

Cited by 24 publications

References 37 publications

Stereoselective and Regioselective Synthesis of Heterocycles via Copper-Catalyzed Additions of Amine Derivatives and Alcohols to Alkenes

Stereoselective and Regioselective Synthesis of Heterocycles via Copper-Catalyzed Additions of Amine Derivatives and Alcohols to Alkenes

Further Developments and Applications of Oxazoline-Containing Ligands in Asymmetric Catalysis

Copper-catalyzed oxidative carbon–heteroatom bond formation: a recent update

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