Synthesis and resolution of 2-methyl-Quinazolinap, a new atropisomeric phosphinamine ligand for asymmetric catalysis

Lacey, Patrick M.; McDonnell, Ciaran; Guiry, Patrick J.

doi:10.1016/s0040-4039(00)00183-0

Cited by 47 publications

(16 citation statements)

References 10 publications

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“…The Pd(PPh 3 ) 4 -catalysed SM cross-coupling reaction between 4-choro-2-methyl-quinazoline 141 and 2-methoxy-1-naphthylboronic acid 139b gave the coupling product 142 which was transformed into enantiopure 2-methylquinazolinap 143, a new atropoisomeric phosphineamine ligand, by other functional group transformations and resolution (Scheme 67). 173 Brown and co-workers reported the synthesis of bridged dimeric isoquinolylnaphthols such as 147 based on a Pd(PPh 3 ) 4 -or Pd 2 (dba) 3 ·CHCl 3 -catalysed SM crosscoupling reaction of the chloroisoquinoline derivative 144 with the substituted binaphthylboronic acid 145 to give a key intermediate 146 followed by sequential functional group transformations (Scheme 68). 174 6.4.…”

Section: Binaphthyl Systemsmentioning

confidence: 99%

Recent applications of the Suzuki–Miyaura cross-coupling reaction in organic synthesis

Kotha¹,

Lahiri²,

Kashinath³

2002

Tetrahedron

1,659

530

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Section: Binaphthyl Systemsmentioning

confidence: 99%

Recent applications of the Suzuki–Miyaura cross-coupling reaction in organic synthesis

Kotha¹,

Lahiri²,

Kashinath³

2002

Tetrahedron

1,659

530

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“…Several research groups have adopted the Ni-catalyzed cross-coupling protocol developed by Cai et al for the synthesis of a wide variety of chiral phosphanes: axially chiral Quinazolinap ligand [28,29], P-stereogenic BINAP [30] and other binaphthyl-based phosphane and phosphite ligands [31]. Figure 9 shows selected examples, such as steroidal [32] and pyrazinylnaphthyl derivatives of BINAP [33], PINAPs [34,35], or fluoroalkyl-tagged binaphthyls [36,37]. Recently, Zhao et al disclosed a method for the cross-coupling of various aryl bromides with diphenylphosphane in the absence of external reductants and supporting ligands (Figure 10) [38].…”

Section: Arylation and Vinylation Of Secondary And Primary Phosphanesmentioning

confidence: 99%

Nickel Complexes in C‒P Bond Formation

et al. 2021

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This review is a comprehensive account of reactions with the participation of nickel complexes that result in the formation of carbon–phosphorus (C‒P) bonds. The catalytic and non-catalytic reactions with the participation of nickel complexes as the catalysts and the reagents are described. The various classes of starting compounds and the products formed are discussed individually. The several putative mechanisms of the nickel catalysed reactions are also included, thereby providing insights into both the synthetic and the mechanistic aspects of this phosphorus chemistry.

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“…This observation led to the development of the 2-methyl-substituted quinazoline 507 which gave improved enantioselectivities in allylic alkylation. [200] …”

Section: Chiral Phosphorus Donormentioning

confidence: 99%

The Development of Bidentate P,N Ligands for Asymmetric Catalysis

2004

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In this review, an attempt is made to systemise the ro √ le which bidentate phosphinamine (P,N) ligands play in asymmetric catalysis. The ligands will be classified, not by the reaction to which their metal complexes have been applied, but by the nature of their donor atoms. In this manner the development of ligand architectural design can be more easily monitored. The asymmetric transformations to which metal complexes of these ligands have been applied include among others, palladium-catalysed allylic substitutions, copper-catalysed 1,4-additions to enones and rhodiumcatalysed hydroboration of vinylarenes. Excellent enantioselectivities, regioselectivities and reactivities have been achieved in each of these processes.

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Synthesis and resolution of 2-methyl-Quinazolinap, a new atropisomeric phosphinamine ligand for asymmetric catalysis

Cited by 47 publications

References 10 publications

Recent applications of the Suzuki–Miyaura cross-coupling reaction in organic synthesis

Recent applications of the Suzuki–Miyaura cross-coupling reaction in organic synthesis

Nickel Complexes in C‒P Bond Formation

The Development of Bidentate P,N Ligands for Asymmetric Catalysis

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