Synthesis and resolution of 1-(2-diphenylphosphino-1-naphthyl)isoquinoline; a PN chelating ligand for asymmetric catalysis.

Alcock, Nathaniel W.; Brown, John M.; Hulmes, David I.

doi:10.1016/s0957-4166(00)80183-4

Cited by 304 publications

(176 citation statements)

References 36 publications

Supporting

Mentioning

175

Contrasting

Unclassified

Order By: Relevance

“…With chiral 'PN' ligand 13 (Table 2, entries 9 and 10) the small and inconclusive differences may be the result of a SKIE. With 'PN' ligand 14 [29] (Table 2, entries 11 and 12) there was again a small difference in stereochemical outcome and the matched manifold is slightly faster with 4 a (ca. 1.4).…”

Section: C: Comparison With Other Ligandsmentioning

confidence: 94%

Memory Effects in Pd-Catalysed Allylic Alkylation: Stereochemical Labelling through Isotopic Desymmetrization

Lloyd‐Jones

Stephen

1998

Chem. Eur. J.

View full text Add to dashboard Cite

Section: C: Comparison With Other Ligandsmentioning

confidence: 94%

Memory Effects in Pd-Catalysed Allylic Alkylation: Stereochemical Labelling through Isotopic Desymmetrization

Lloyd‐Jones

Stephen

1998

Chem. Eur. J.

View full text Add to dashboard Cite

“…This field has been reviewed recently. [8] The present paper is concerned with comparisons between ligands of the type 1,1'-(2-diarylphosphino-1-naphthyl)isoquinoline ligands [9] involved in Rh-complex-catalysed asymmetric hydroboration, and in the effects of the aryl substituents on the efficiency and enantiomer excess observed.…”

Section: Introductionmentioning

confidence: 99%

The Scope of Catalytic Asymmetric Hydroboration/Oxidation with Rhodium Complexes of 1,1′‐(2‐Diarylphosphino‐1‐naphthyl)isoquinolines

Doucet

Fernández

Layzell

et al. 1999

Chemistry A European J

Self Cite

173

View full text Add to dashboard Cite

Preformed cationic Rh complexes of the title ligands are effective for the asymmetric hydroboration/oxidation of vinylarenes at ambient temperature. These vinylarenes may carry E-or Z-b substituents but not a substituents. Enantiomer excesses of up to 97 % can be obtained in the most favourable cases. The enantioselectivity is moderately sensitive to the structure of the ligand: the difurylphosphino ligand gave superior results for electron-poor styrenes and the diphenylphosphino ligand the best results for electron-rich reactants. Mechanistic aspects are discussed.

show abstract

“…alpha arylation | heterocycle | isoquinoline-N-oxide | one-pot T he isoquinoline motif and its derivatives form the cores of numerous natural products (1,2), are the central components of a number of pharmaceutical agents (3)(4)(5), and can provide the scaffold for chiral ligands (6,7) and valuable organic materials (8). However, traditional isoquinoline syntheses such as the Bischler-Napieralski (9, 10), Pictet-Spengler (11,12), and Pomeranz-Fritsch reactions (13)(14)(15) all centre around the lynchpin of electrophilic aromatic substitution and are thus often limited to electron-rich carbocycles (Scheme 1A).…”

mentioning

confidence: 99%

Synthesis of substituted isoquinolines utilizing palladium-catalyzed α-arylation of ketones

Donohoe

Pilgrim

Jones

et al. 2012

Proc. Natl. Acad. Sci. U.S.A.

View full text Add to dashboard Cite

The utilization of sequential palladium-catalyzed α-arylation and cyclization reactions provides a general approach to an array of isoquinolines and their corresponding N-oxides. This methodology allows the convergent combination of readily available precursors in a regioselective manner and in excellent overall yields. This powerful route to polysubstituted isoquinolines, which is not limited to electron rich moieties, also allows rapid access to analogues of biologically active compounds.T he isoquinoline motif and its derivatives form the cores of numerous natural products (1, 2), are the central components of a number of pharmaceutical agents (3-5), and can provide the scaffold for chiral ligands (6, 7) and valuable organic materials (8). However, traditional isoquinoline syntheses such as the Bischler-Napieralski (9, 10), 12), and Pomeranz-Fritsch reactions (13-15) all centre around the lynchpin of electrophilic aromatic substitution and are thus often limited to electron-rich carbocycles (Scheme 1A). It is also imperative to develop routes to highly-substituted isoquinolines to fully explore this chemical space, for example, for potential pharmaceutical targets. While recent synthetic efforts have greatly expanded the diversity of isoquinoline motifs available (16-29), new routes to isoquinolines are still highly desirable, particularly ones with the ability to directly access the isoquinoline moiety in a range of oxidation levels and which do not require highly-specialized starting materials.Originally reported by Palucki and Buchwald (30), Hamann and Hartwig (31), and Miura and coworkers (32), the palladiumcatalyzed α-arylation of enolates has recently emerged as a powerful new reaction in synthetic organic chemistry (33-35). Key to its success has been the design of appropriate ligands for palladium that have precisely engineered steric and electronic properties to enable the various steps in the catalytic cycle to proceed with maximum efficiency (36-39). The reaction's utility has also been greatly enhanced by the development of robust preformed palladium catalysts. Properties such as air stability and very high reactivity in a range of systems have greatly expanded the potential uses of these catalysts (40-43). However, the α-arylation reaction has seen limited use in the de novo construction of aromatic compounds (44-51) and is still greatly underused in this regard, especially because the bond forming abilities provided by this powerful reaction can greatly simplify the design of routes to heavily-substituted aromatic compounds. Hence, we decided to explore the scope of this new catalytic method in the synthesis of important heteroaromatic ring systems, beginning our investigations with the isoquinoline nucleus. ResultsIn our disconnection approach we envisaged that key pseudo-1,5-dicarbonyl intermediates 3 could be accessed via the palladiumcatalyzed α-arylation of ketones 1 with aryl halides 2 possessing a protected aldehyde or ketone in the ortho-position (52). Subsequent treatment of these inter...

show abstract

Synthesis and resolution of 1-(2-diphenylphosphino-1-naphthyl)isoquinoline; a PN chelating ligand for asymmetric catalysis.

Cited by 304 publications

References 36 publications

Memory Effects in Pd-Catalysed Allylic Alkylation: Stereochemical Labelling through Isotopic Desymmetrization

Memory Effects in Pd-Catalysed Allylic Alkylation: Stereochemical Labelling through Isotopic Desymmetrization

The Scope of Catalytic Asymmetric Hydroboration/Oxidation with Rhodium Complexes of 1,1′‐(2‐Diarylphosphino‐1‐naphthyl)isoquinolines

Synthesis of substituted isoquinolines utilizing palladium-catalyzed α-arylation of ketones

Contact Info

Product

Resources

About