Asymmetric Epoxidation of Electron-Deficient Olefins

Díez, David; Núñez, Marta G.; Antón, Ana B.; Garcı́a, Pilar Garcı́a; Moro, Rosalina F.; Garrido, Narciso M.; Marcos, Isidro S.; Basabe, P.; Urones, Julio G.

doi:10.2174/157017908785133429

Cited by 98 publications

(27 citation statements)

References 3 publications

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“…All products were characterized by NMR and mass spectrometry. The epoxidation of the electron-poor C=C double bond [27,28] was carried out, adapting to the case of prochiral BPs the classical Weitz-Scheffer reaction for the epoxidation of α,β-unsaturated aldehydes, consisting of the use of hydrogen peroxide as the oxidant under basic conditions [29]. The use of H 2 O 2 is recommended due to its highly environmentally acceptable character [30] and involves the nucleophilic attack of HOO − generated in situ to the electron-poor C=C double bond.…”

Section: Resultsmentioning

confidence: 99%

Organocatalytic Enantioselective Epoxidation of Some Aryl-Substituted Vinylidenebisphosphonate Esters: On the Way to Chiral Anti-Osteoporosis Drugs

Chiminazzo¹,

Sperni²,

Scarso³

et al. 2017

Catalysts

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Abstract:The synthesis of a new class of epoxide derivatives from prochiral vinylidene bisphosphonate (VBP) precursors is reported using hydrogen peroxide as the terminal oxidant. The reaction is carried out using a series of possible organic activators having a basic character, with the best results being observed using quinine and sparteine. These activators not only provide from good to excellent epoxide yields with a large variety of VBPs, but also interesting enantioselectivities in the 67%-96% ee range, at least in the case of the Ph and m-MeO-Ph VBP derivatives, opening the way to a number of chiral anti-osteoporosis potentially active pharmaceutical ingredients.

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Section: Resultsmentioning

confidence: 99%

Organocatalytic Enantioselective Epoxidation of Some Aryl-Substituted Vinylidenebisphosphonate Esters: On the Way to Chiral Anti-Osteoporosis Drugs

Chiminazzo¹,

Sperni²,

Scarso³

et al. 2017

Catalysts

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“…The epoxidation of the electron-poor C=C double bond [27,28] was carried out, adapting to the case of prochiral BPs the classical Weitz-Scheffer reaction for the epoxidation of α,β-unsaturated aldehydes, consisting of the use of hydrogen peroxide as the oxidant under basic conditions [29]. The use of H2O2 is recommended due to its highly environmentally acceptable character [30] and involves the nucleophilic attack of HOO − generated in situ to the electron-poor C=C double bond.…”

Section: Resultsmentioning

confidence: 99%

Organocatalytic Stereoselective Epoxidation of Aryl-Substituted Vinylidenebisphosphonate Esters: On the Way to Chiral Anti-Osteoporosis Drugs

Chiminazzo¹,

Sperni²,

Scarso³

et al. 2017

Preprint

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“…[55][56][57] In 1980, Julia and co-workers 58 reported on the first highly enantioselective epoxidation (in >90% ee) of chalcones catalyzed by polyamino acids (Scheme 35.22). 59 Typically, the reaction was carried out under mild conditions in a triphasic system (toluene, water, and polymer catalyst) using hydrogen peroxide as an oxidant.…”

Section: Nucleophilic Epoxidationsmentioning

confidence: 99%

Asymmetric Epoxidation in Stereoselective Synthesis

Yang

2013

Stereoselective Synthesis of Drugs and Natural Products

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Asymmetric epoxidation of olefins has been proven to be one of the most important methods to generate chiral epoxides, which are highly useful intermediates in the stereoselective synthesis of biologically interesting compounds. In this chapter, several powerful and practical asymmetric epoxidation methods and their utilities for the stereoselective synthesis of drug substances and natural products are described. The representative asymmetric epoxidation methods that are described in the chapter include directed epoxidations, metal oxo‐catalyzed epoxidations, dioxirane‐catalyzed epoxidations, nucleophilic epoxidations, and asymmetric phase‐transfer–catalyzed epoxidations.

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Asymmetric Epoxidation of Electron-Deficient Olefins

Cited by 98 publications

References 3 publications

Organocatalytic Enantioselective Epoxidation of Some Aryl-Substituted Vinylidenebisphosphonate Esters: On the Way to Chiral Anti-Osteoporosis Drugs

Organocatalytic Enantioselective Epoxidation of Some Aryl-Substituted Vinylidenebisphosphonate Esters: On the Way to Chiral Anti-Osteoporosis Drugs

Organocatalytic Stereoselective Epoxidation of Aryl-Substituted Vinylidenebisphosphonate Esters: On the Way to Chiral Anti-Osteoporosis Drugs

Asymmetric Epoxidation in Stereoselective Synthesis

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