Naphthyl-substituted bisoxazoline and pyridylbisoxazoline–copper(I) catalysts for asymmetric allylic oxidation

Zhou, Ziniu; Andrus, Merritt B.

doi:10.1016/j.tetlet.2012.06.010

Cited by 28 publications

(9 citation statements)

References 39 publications

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“… 11 The β-amino alcohol 5 was further transformed into 1-naphthyl-substituted bisoxazoline ligand 6 in 74% yield by reaction with dimethylmalononitrile and Zn(OTf) 2 . 11a , 12 Furthermore, aryl iodide and different N -alkyl substituted substrate 1ae was well tolerated under the established reaction conditions ( Scheme 4c ). Hydrogenation of 1ae using ( S , S )-SINpEt·HBF 4 as the carbene ligand precursor, furnished the oxazolidinone 2ae (92% ee and 96% yield), a key synthetic intermediate employed in the synthesis of the alkaloid (–)-aurantioclavine.…”

Section: Resultsmentioning

confidence: 88%

Enantioselective synthesis of 2-oxazolidinones by ruthenium(ii)–NHC-catalysed asymmetric hydrogenation of 2-oxazolones

Wollenburg

Glorius

2018

Chem. Sci.

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Section: Resultsmentioning

confidence: 88%

Enantioselective synthesis of 2-oxazolidinones by ruthenium(ii)–NHC-catalysed asymmetric hydrogenation of 2-oxazolones

Wollenburg

Glorius

2018

Chem. Sci.

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“…Using ligand 781 and CuPF 6 the corresponding product was isolated in 40% yield and 80% ee , while use of ligand 782 gave the product in 80% yield and 85% ee . 299 …”

Section: Bis(oxazoline) Ligandsmentioning

confidence: 99%

“…Andrus and Zhou prepared two regioisomers of naphthyl-substituted BOX ligands ( 781 and 782 ) and screened them in the allylic oxidation of cyclohexene 819 (Scheme ). Using ligand 781 and CuPF 6 the corresponding product was isolated in 40% yield and 80% ee , while use of ligand 782 gave the product in 80% yield and 85% ee …”

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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“…Katsuki later discovered that cyclopentene could be converted to allylic ester 7 in 93% ee using a modified C 3 -symmetric trisoxazoline ligand 9 (Scheme B) . While various other ligand classes have been examined in the asymmetric Kharasch–Sosnovsky reaction, bisoxazoline ligands have shown the highest enantioselectivity to date. − For example, Andrus utilized ligand 11 to form allylic ester 10 in 99% ee (Scheme C) …”

Section: Asymmetric Kharasch–sosnovsky Reaction With Unactivated Cycl...mentioning

confidence: 99%

Catalytic Asymmetric Intermolecular Allylic Functionalization of Unactivated Internal Alkenes

Bayeh

Tambar

2017

ACS Catal.

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The asymmetric allylic functionalization of unactivated internal alkenes is an emerging strategy for the conversion of simple unsaturated starting materials into a diverse range of enantioenriched products. This Perspective summarizes the development of reactions wherein a chiral catalyst facilitates the intermolecular stereoselective reaction between an achiral unactivated internal alkene and a reagent.

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Naphthyl-substituted bisoxazoline and pyridylbisoxazoline–copper(I) catalysts for asymmetric allylic oxidation

Cited by 28 publications

References 39 publications

Enantioselective synthesis of 2-oxazolidinones by ruthenium(ii)–NHC-catalysed asymmetric hydrogenation of 2-oxazolones

Enantioselective synthesis of 2-oxazolidinones by ruthenium(ii)–NHC-catalysed asymmetric hydrogenation of 2-oxazolones

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

Catalytic Asymmetric Intermolecular Allylic Functionalization of Unactivated Internal Alkenes

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