Nickel-Catalyzed Asymmetric Kumada Cross-Coupling of Symmetric Cyclic Sulfates

Eno, Meredith S.; Lu, Alexander; Morken, James P.

doi:10.1021/jacs.6b03384

Cited by 45 publications

(18 citation statements)

References 75 publications

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“…A range of aryl Grignard reagents 1314 were successfully coupled with the cyclic sulfates 1313 to give, following acid hydrolysis, chiral alcohols 1315 in up to 98% yield and with high enantioselectivities up to 92% ee ( Scheme 389 ). 465 …”

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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Section: Bis(oxazoline) Ligandsmentioning

confidence: 99%

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

et al. 2021

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“…(5S,9R)-5,9-二甲基十五烷( 46)是咖啡潜叶蛾(Perileucoptera coffeella)性信息素的主要活性成分 [74][75] . Poppe 等 [76] [77] , 由于格氏试剂易合成、成本低、活性好, 该反应为构建碳碳键开辟了一条简捷、高效的途径, 是目前有机合成研究领域的热点 [78][79] . (10R,14R)-10,14-二甲基-1-十八碳烯( 47) 是苹果银纹潜叶蛾(Lyonetia prunifoliella)性信息素的主要活性成分 [80][81] ; 也有研究表明, 其对映体(10S,14S)-47 具有吸引日本与朝鲜苹果银纹潜叶蛾雄虫的生理活性 [82][83] .…”

Section: Wittig 偶联法unclassified

Research Progress on the Syntheses of Chiral Methyl-Branched Aliphatic Hydrocarbons Insect Pheromones

Yuan¹,

Bian²,

Wang³

et al. 2021

Chinese Journal of Organic Chemistry

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The chiral methyl-branched aliphatic hydrocarbon insect pheromones including single, double and multichiral methyl-branched insect pheromones are the most promising green control of Scoliopteryx libatrix, Monochamus titillator, Lyonetia clerkella and other many pests. The syntheses of single chiral methyl-branched pheromones are reviewed according to the methods of constructing chiral methyl, whereas the preparation of double chiral methyl-branched and multichiral methyl-branched ones are illustrated on the basis of the linking strategies of the key fragments. Moreover, the advantages and disadvantages of the synthetic approaches are discussed, as well as the prospects for the synthesis of chiral methyl-branched aliphatic hydrocarbon insect pheromones.

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“…So far, alkyl halides have been developed to be efficient alkyl sources in C sp3 −C bond formation reactions . In addition, a series of alkyl electrophiles, including cyclic anhydrides, alkyl ethers, styrenyl epoxides even styrenyl aziridines, and cyclic sulfates, have also been successfully exploited to construct C sp3 −C bonds. Recently, redox‐active esters derived from alkyl carboxylic acids and N ‐hydroxyphthalimide (NHPI) were demonstrated to be very efficient alkyl electrophiles in alkyl cross‐coupling reactions .…”

Section: Figurementioning

confidence: 99%

Visible‐Light‐Mediated Dual Decarboxylative Coupling of Redox‐Active Esters with α,β‐Unsaturated Carboxylic Acids

Zhang

Yang

Guo

et al. 2017

Chemistry A European J

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An efficient visible-light-induced decarboxylative coupling between α,β-unsaturated carboxylic acids and alkyl N-hydroxyphthalimide esters has been developed. A wide range of redox-active esters derived from aliphatic carboxylic acids (1°, 2° and 3°) proved viable in this dual decarboxylation process, affording a broad scope of substituted alkenes in moderate to excellent yields with good E/Z selectivities. This redox-neutral procedure was highlighted by its mild conditions, operational simplicity, easy accessibility of carboxylic acids, and excellent functional-group tolerance.

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Nickel-Catalyzed Asymmetric Kumada Cross-Coupling of Symmetric Cyclic Sulfates

Cited by 45 publications

References 75 publications

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

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

Research Progress on the Syntheses of Chiral Methyl-Branched Aliphatic Hydrocarbons Insect Pheromones

Visible‐Light‐Mediated Dual Decarboxylative Coupling of Redox‐Active Esters with α,β‐Unsaturated Carboxylic Acids

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