Facile syntheses of aryldifluorophosphonate building blocks

Cockerill, G. Stuart; Easterfield, Howard J.; Percy, Jonathan M.

doi:10.1016/s0040-4039(99)00266-x

Cited by 21 publications

(7 citation statements)

References 13 publications

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“…Percy et al . used different reaction conditions [Zn/Cu, Pd[P( o ‐tol) 3 ] 2 Cl 2 in toluene and dimethylacetamide (DMA)] to obtain 200 in 36% yield [156] . This synthetic route was further employed for the preparation of derivatives containing an additional functional group on the aromatic ring as shown in Scheme 75b.…”

Section: Asymmetric Construction Of Amino Acid Fluorophosphonate Derimentioning

confidence: 99%

Asymmetric Synthesis of Chiral Amino Carboxylic‐Phosphonic Acid Derivatives

Cahard

Cao

et al. 2020

Adv Synth Catal

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Chiral amino acids featuring a phosphonate pendant arm are an important type of biologically active scaffold. Here in this review, we comprehensively summarize the modern synthetic methods towards asymmetric construction of chiral amino carboxylic‐phosphonic acid derivatives. The main streams of such interesting compounds include phosphono‐containing α‐, β‐, and γ‐amino acid derivatives, amino acid fluorophosphonate derivatives, amino acid cyclopropanylphosphonate derivatives, and bisphosphono‐amino acid derivatives. Chiral resolution protocols, chiral auxiliary‐directed syntheses, and valorization of the pool of abundant chiral amino acid resources remain contemporary concerns, and meanwhile catalytic enantioselective synthesis has also emerged as a potent strategy as demonstrated by the latest advances.magnified image

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Section: Asymmetric Construction Of Amino Acid Fluorophosphonate Derimentioning

confidence: 99%

Asymmetric Synthesis of Chiral Amino Carboxylic‐Phosphonic Acid Derivatives

Cahard

Cao

et al. 2020

Adv Synth Catal

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“…22,23 Modern methods for the generation of molecular diversity have not to our knowledge been deployed extensively in this area of chemistry-the attempts by Ganesan 24 and Bergnes 25 to synthesise libraries of phosphate mimetics as potential phosphatase inhibitors provide rare examples and illustrate the need for readily-available functionalised scaffolds bearing phosphate mimetics. Following our recent communication in this area, 26 we wish to describe the scope, generality and limitations of palladium-catalysed coupling reactions investigated in our laboratory.…”

mentioning

confidence: 99%

Facile syntheses of building blocks for the construction of phosphotyrosine mimetics

Cockerill¹,

Easterfield

Percy

et al. 2000

J. Chem. Soc., Perkin Trans. 1

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The copper-catalysed zinc phosphonate chemistry described by Yokomatsu and Shibuya can be used to enter the classical organometallic coupling repertoire via Stille and Suzuki–Miyaura couplings. 1,4-Diiodobenzene underwent coupling with the organozinc reagent derived from diethyl bromodifluoromethylphosphonate with copper(I) catalysis to afford diethyl (4-iodophenyl)difluoromethylphosphonate. Higher yielding couplings were run with (4-trifluoromethylsulfonyloxy)- and (4-nonafluorobutylsulfonyloxy)-iodobenzenes. The iodide and the triflate coupled under palladium-catalysed conditions with a range of stannanes and boronic acids in moderate to excellent yields. Shibuya–Yokomatsu couplings were also successful with more functionalised iodoarenes and heteroarenes presenting the important phosphate mimic on a range of scaffolds

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“…Cyclization reactions have been used to produce substituted benzo[b]furans [270][271][272] Fig. (42).…”

Section: Benzofuransmentioning

confidence: 99%