Enantioselective Hydrophosphonylation of <i>in Situ</i> Generated <i>N</i>-Acyl Ketimines Catalyzed by BINOL-Derived Phosphoric Acid

Suneja, Arun; Unhale, Rajshekhar A.; Singh, Vinod K.

doi:10.1021/acs.orglett.6b03623

Cited by 66 publications

(24 citation statements)

References 66 publications

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“…Singh et al. reported an enantioselective synthesis of isoindolinone‐based α‐aminophosphonates with a quaternary stereogenic center catalyzed by a chiral phosphoric acid (Scheme ) . The hydrophosphonylation of in situ generated ketimines derived from isoindolinones 211 worked well in the presence of 10 mol% of 213 , giving products 212 in good yields and ee values.…”

Section: Direct Phosphorylation Of the Parent Heterocyclesmentioning

confidence: 99%

Recent Advances in the Construction of Phosphorus‐Substituted Heterocycles, 2009–2019

2020

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Scheme 20. Phosphonation of pyridinones.Scheme 21. CuI-catalyzed phosphoramidate formation.Scheme22. Phosphonation of coumarin and quinolinone.Scheme23. Silver(I)-catalyzed phosphonation of coumarins. Scheme 33. Electrochemical C(sp 2 )ÀHphosphonation of quinoxaline-2(1H)-ones. Scheme 39. Phosphorylation of quinoxaline-2(1 H)-ones. Scheme40. Autoxidative phosphorylation of quinoxalines. Scheme 41. DTBP-mediated formation of phosphonated benzothiazoles. Scheme42. Phosphonation of imidazole[2,1-b]thiazoles.Scheme 47. Copper(I)-catalyzedp hosphonationo fN-iminoisoquinolinium ylides. Scheme48. Aerobic phosphonationofC ( sp 3 ) À Hbonds. Scheme 49. Copper(II)/PBQ-catalyzed phosphorylation of 3,4-dihydro-1,4-benzoxazin-2-ones. Scheme 87. Asymmetric exo-selective [3+ +2] cycloaddition to afford phosphorus-substituted pyrrolidines. Scheme 95. Cascade condensation/cyclization to phosphonylated thienopyridines. Scheme 96. S N Ar'-involved cascade reactions to phosphonylated oxygenorn itrogen heterocycles.Scheme 97. Manganese(III)-mediated synthesis of 3-phosphonyldihydrofuransfrom b-ketophosphonates.Scheme98. Cyclization to phosphonated isochromenes.Scheme 121. Asymmetric [4+ +2] cycloaddition of b,g-unsaturated a-ketophosphonates.

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Section: Direct Phosphorylation Of the Parent Heterocyclesmentioning

confidence: 99%

Recent Advances in the Construction of Phosphorus‐Substituted Heterocycles, 2009–2019

2020

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“…Moreover, isoindolinone bearing a heterocyclic ring such as furan at C‐3 could also afford the desired α‐amino phosphonate successfully. The reaction also proceeded smoothly at ambient temperature, forming several interesting valuable synthetic intermediates (Scheme C) …”

Section: Enantioselective Synthesis Of Isoindolinones By Using Organomentioning

confidence: 99%

“…Moreover,i soindolinone bearing ah eterocyclic ring such as furan at C-3 could also afford the desired a-aminop hosphonate successfully.T he reactiona lso proceeded smoothly at ambient temperature, forming several interesting valuables ynthetic intermediates (Scheme 8C). [27] a-Diazocarbonyl compounds are important structural motifs in synthetic organic chemistry. [28] In 2018, [29a] Singh and coworkers established an asymmetric Mannich-type process employing a-diazo esters as the nucleophiles under ambient conditions (Scheme 9).…”

Section: Other Nucleophilic Reagentsmentioning

confidence: 99%

Catalytic Asymmetric Synthesis of Isoindolinones

Gao

Chen

Ding

et al. 2019

Chemistry An Asian Journal

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As important reactive species, isoindolinones represent a cluster of valuable building blocks for the construction of natural‐product‐like compounds. In particular, chiral isoindolinones are the key structural feature of naturally occurring bioactive molecules. During the past decade, great advances have been made in the asymmetric synthesis of isoindolinone skeleton compounds. Hence, recent progress in catalytic asymmetric synthesis of isoindolinones is reviewed here, with emphasis on chiral organocatalysis and transition metal complexes enabled transformations. Different organocatalysts (chiral phosphoric acids, phase transfer catalysts, chiral thioureas) and chiral transition‐metal complexes (Rh, Pd, Ir, Cu, Mg, and Ni) are included in this transformation.

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“…Continuing on this theme, the Singh group attempted the asymmetric hydrophosphonylation of 2f . Under the catalysis of ( S ) ‐ BINOL‐based phosphoric acid Cat.…”

Section: Use Of Cyclic Imines 2 Bearing a 1h‐isoindole Moietymentioning

confidence: 99%

Organocatalytic Asymmetric Transformations Involving the Cyclic Imine Moiety in Indole and Isoindole Related Heterocycles

Cheng

Shao

2018

Adv Synth Catal

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Scheme 8. Asymmetric Mannichr eaction of 2-aryl-3H-indol-3-ones 1c with aldehydes and ketones catalyzed by l-proline. Scheme 12. Catalytic asymmetric aza-DAr eaction of 2-aryl-3H-indol-3-ones 1c with 2,4-dienals 34 via trienaminec atalysis. Scheme 18. Enantioselective[ 4 + +2] cycloaddition of ketimines 2a or 2b with allenoate 53a catalyzed by (R)-SITCP Cat. 18. Scheme 34. Bifunctional phosphine Cat. 31-catalyzed stepwise [4+ +2]/[2+ +2] cycloadditions between allene ketones 96 and 2d.

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Enantioselective Hydrophosphonylation of in Situ Generated N-Acyl Ketimines Catalyzed by BINOL-Derived Phosphoric Acid

Cited by 66 publications

References 66 publications

Recent Advances in the Construction of Phosphorus‐Substituted Heterocycles, 2009–2019

Recent Advances in the Construction of Phosphorus‐Substituted Heterocycles, 2009–2019

Catalytic Asymmetric Synthesis of Isoindolinones

Organocatalytic Asymmetric Transformations Involving the Cyclic Imine Moiety in Indole and Isoindole Related Heterocycles

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