Recent Synthesis and Transformation of Vinylphosphonates

Dembitsky, Valery M.; Quntar, Abed Al Aziz Al; Haj‐Yehia, Abdullah; Srebnik, Morris

doi:10.2174/1570193052774090

Cited by 71 publications

(21 citation statements)

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“…[50] This new versatile building block could be involved in a variety of synthetic transformations such as ozonolysis, cycloaddition, conjugate addition or methyl ketone formation. [16,51] Proposed transition-state model: The determination of the absolute configuration allowed us to postulate a Michael acceptor attack from the Si face of the (E)-enamine according to steric shielding (Scheme 15).…”

Section: Determination Of the Ee Of G-gem-phosphonate Aldehydesmentioning

confidence: 99%

“…[15] Moreover, despite the great interest in vinyl phosphonates, [16] few reports describe the formation of chiral g-phosphonate carbonyl compounds through ACA. [17] With a view to generalizing the scope of pyrrolidine-based catalysis, we have recently communicated the first enantioselective organocatalytic conjugate addition of aldehydes to vinyl sulfones [18] and to vinyl phosphonates [19] (Scheme 1).…”

Section: Introductionmentioning

confidence: 99%

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Enantioselective Organocatalytic Conjugate Addition of Aldehydes to Vinyl Sulfones and Vinyl Phosphonates as Challenging Michael Acceptors

Sulzer‐Mossé

Alexakis

Mareda

et al. 2009

Chemistry A European J

160

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Chiral framework: Chiral amines with pyrrolidine frameworks catalyze the enantioselective conjugate addition of a wide range of aldehydes to various vinyl sulfones and vinyl phosphonates in high yields and with enantioselectivities up to >99 % ee (see scheme). The high versatility of the Michael adducts is exemplified by various functionalizations with conservation of the optical purity.Chiral amines with a pyrrolidine framework catalyze the enantioselective conjugate addition of a broad range of aldehydes to various vinyl sulfones and vinyl phosphonates in high yields and with enantioselectivities up to >99 % ee. This novel process provides synthetically useful chiral gamma-gem-sulfonyl or phosphonyl aldehydes which can be widely functionalized with retention of the enantiomeric excess. Mechanistic insights including DFT calculations are explored in detail.

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Section: Determination Of the Ee Of G-gem-phosphonate Aldehydesmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Enantioselective Organocatalytic Conjugate Addition of Aldehydes to Vinyl Sulfones and Vinyl Phosphonates as Challenging Michael Acceptors

Sulzer‐Mossé

Alexakis

Mareda

et al. 2009

Chemistry A European J

160

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“…Arylphosphonates are the phosphonic acids precursors, which can be used for their water-soluble properties and for the synthesis of mixed organic-inorganic materials [44,45]. Vinylphosphonates are a well-known class of organophosphorus compounds that are very useful intermediates for the construction of many synthetically and pharmaceutically important compounds including acyclic, carbocyclic, and especially heterocyclic compounds, b-aminophosphonates and 1,2-epoxyalkylphosphonates [46,47]. Terminal vinylphosphonates (1-aryl or 1-alkyl ethenylphosphonates) are used as precursors for the synthesis of optically active 1-aryl-or 1-alkyl-substituted ethylphosphonates by asymmetric reduction [48].…”

Section: Applications Of the Hirao Productsmentioning

confidence: 99%

Microwave-assisted Hirao reaction: recent developments

Brahmachari

2015

ChemTexts

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Organic molecules containing phosphorus, now, constitute a major branch of chemistry, and offer fascinating possibilities for their structural, synthetic, and mechanistic study as well as promising biological activities. Organophosphorus compounds find numerous potential applications in the areas of industrial, agricultural, and medicinal chemistry. Aryl-and vinyl-phosphonates are an important class of organophosphorus compounds with potential biological relevance. The Hirao reaction offers a way to access these compounds through phosphorus-carbon (P-C) cross-coupling of aryl and vinyl halides with O,O-dialkyl phosphites, and this reaction has attained a commendable development in many ways in regard to the diversity in the substrates, [P(O)H species, catalysts, and reaction conditions. The present article deals with such developments that occurred under the influence of microwave irradiation.

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“…Alkenyl-phosphorus compounds bearing a vinyl group attached to the phosphorus center are an important class of chemicals which are used extensively in pharmaceuticals and material sciences [156][157][158]. Scheme 25 depicts a new synthetic approach to vinylphosphonates, utilizing Ni(0)-catalysis [159].…”

Section: Cu- Ni- and Other Metal-catalyzed Reactionsmentioning

confidence: 99%

Recent Advances in H-Phosphonate Chemistry. Part 2. Synthesis of C-Phosphonate Derivatives

Sobkowski

Kraszewski

Stawiński

2014

Phosphorus Chemistry II

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This chapter provides an overview of recent advances in the development of new methods and protocols for the formation of the P-C bond using H-phosphonate diesters as starting materials. Various chemical and stereochemical aspects of the transition metal-catalyzed cross-coupling and organocatalyst-promoted reactions which are relevant to the synthesis of structurally diverse C-phosphonate derivatives are surveyed.

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Recent Synthesis and Transformation of Vinylphosphonates

Cited by 71 publications

References 0 publications

Enantioselective Organocatalytic Conjugate Addition of Aldehydes to Vinyl Sulfones and Vinyl Phosphonates as Challenging Michael Acceptors

Enantioselective Organocatalytic Conjugate Addition of Aldehydes to Vinyl Sulfones and Vinyl Phosphonates as Challenging Michael Acceptors

Microwave-assisted Hirao reaction: recent developments

Recent Advances in H-Phosphonate Chemistry. Part 2. Synthesis of C-Phosphonate Derivatives

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