Improved procedure for Juliá–Colonna asymmetric epoxidation of α,β-unsaturated ketones: total synthesis of diltiazem and Taxol TM side-chain

Adger, B. M.; Barkley, James V.; Bergeron, Sophie; Cappi, Michael W.; Flowerdew, Benjamin E.; Jackson, Mark; McCague, Raymond; Nugent, Thomas C.; Roberts, Stanley M.

doi:10.1039/a704413e

Cited by 138 publications

(23 citation statements)

References 18 publications

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“…Gerlach and Geller [71] have reported the process development studies that allow the reaction to be run on pilot plant scale. The resulting epoxides can be converted into a wide range of interesting products, [72] …”

Section: The Juliá -Colonna Methods (Polyleucine Oxidation)mentioning

confidence: 99%

Industrial Catalysts for Regio‐ or Stereo‐Selective Oxidations and Reductions. A Review of Key Technologies and Targets

Whittall

2007

Regio‐ and Stereo‐ Controlled Oxidations and Reductions

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Section: The Juliá -Colonna Methods (Polyleucine Oxidation)mentioning

confidence: 99%

Industrial Catalysts for Regio‐ or Stereo‐Selective Oxidations and Reductions. A Review of Key Technologies and Targets

Whittall

2007

Regio‐ and Stereo‐ Controlled Oxidations and Reductions

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“…-Hydroxysulfide moiety is present in compounds of biological and pharmacological interest [75] and is a versatile group for synthesizing allylic alcohols [76], benzoxathiepi- [77], benzotiazepines [78], -thioketones [79], -substituted -unsaturated enones [80], and -hydroxysulfoxides used in the synthesis of naturally occurring compounds [81]. The easiest access to -hydroxysulfides is the reaction of epoxides with thiols catalyzed by bases [82] or acids [83].…”

Section: Preparation Of -Hydroxythioethersmentioning

confidence: 99%

Cesium and Aluminum Salts of Dodecatungstophosphoric Acid as Eco-Friendly and Efficient Heterogeneous Catalysts in Organic Synthesis: Some Recent Advances

Firouzabadi¹,

Jafari

2008

COC

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In this review we have paid attention to cesium and aluminum salts of dodecatungstophosphoric acid as ecofriendly and efficient heterogeneous catalysts. The structural effect and also catalytic properties of exchanging Cs + with protons in dodecatungstophosphoric acid is discussed. Using cesium and aluminum salts of dodecatungstophosphoric acid as efficient catalysts for Friedel-Crafts reactions such as acylation and alkylation of aromatic compounds, Fries, Claisen and pinacol rearrangements, esterification, amidation, ether formation, protection of thiols, alcohols and amines, conversion of aldehydes to their acylals, ring opening of epoxides, selective protection of one hydroxy group in diols, preparation of -hydroxythioethers and regioselective bromination of aromatic compounds are discussed.

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“…For example, Roberts optimized the conditions and achieved a two-phase system that consisted of anhydrous THF as the solvent, a soluble urea-hydrogen peroxide complex (UHP) as the oxygen source, and 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) as a soluble base [60]. Alternatively, sodium percarbonate in a dimethylformamide (DMF)-water mixture could be successfully and conveniently used as a source of base and oxidant [61].…”

Section: Polyamino Acidsmentioning

confidence: 99%

Asymmetric Epoxidations of α,β‐Unsaturated Carbonyl Compounds

Lattanzi

2010

Catalytic Asymmetric Conjugate Reactions

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The asymmetric epoxidation of alkenes is a fundamental process in organic synthesis, and unquestionably the most exploited approach to synthesize epoxides [1]. Alternative useful strategies to access these molecules concern the enantioselective alkylidenation of carbonyl compounds by ylides [2] and the Darzens condensation [3]. Enantioenriched epoxides are important targets of biological and pharmaceutical interest. Moreover, their high synthetic potential as intermediates is exemplified by the stereoselective ring opening with nucleophiles, which affords a variety of compounds with two contiguous chiral centers, the absolute configuration of which can be controlled [4].During the past few decades, metal-based electrophilic asymmetric methodologies of epoxidation have been successfully developed and found widespread application in multistep synthesis; these include: the Sharpless' epoxidation of allylic alcohols mediated by the Ti/tartrate system [5]; and the Jacobsen's and Katsuki's epoxidation of unfunctionalized alkenes by using Mn-and Ti-/Salen complexes [6]. More recently, chiral Ru-Pt and Fe-Pt complexes have proved to be effective in the enantioselective epoxidation of disubstituted aromatic and challenging terminal unfunctionalized alkenes [7]. Impressive results have been achieved by the groups of Yang [8] and Shi [9] for the electrophilic organocatalyzed asymmetric epoxidation of a great variety of olefins such as trisubstituted, disubstituted trans-alkenes, terminal alkenes, dienes, and enynes (to cite the most relevant examples), and by the in situ generation of dioxiranes derived from chiral ketones. Within the context of asymmetric epoxidation catalyzed by organic promoters, notable achievements have also been attained by using chiral oxaziridines [10], oxaziridinium salts [11], amines [12], and peptide-based peracids [13].The epoxidation of α,β-unsaturated carbonyl compounds leads to the formation of another valuable class of functionalized epoxides [14], the carbonyl and epoxide groups of which can be selectively manipulated to provide enantioenriched products such as allylic epoxy alcohols, α-or β-hydroxy ketones, and α,β-epoxy esters [15]. The general approach for the epoxidation of electron-poor Catalytic Asymmetric Conjugate Reactions. Edited by Armando Córdova

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Improved procedure for Juliá–Colonna asymmetric epoxidation of α,β-unsaturated ketones: total synthesis of diltiazem and Taxol TM side-chain

Cited by 138 publications

References 18 publications

Industrial Catalysts for Regio‐ or Stereo‐Selective Oxidations and Reductions. A Review of Key Technologies and Targets

Industrial Catalysts for Regio‐ or Stereo‐Selective Oxidations and Reductions. A Review of Key Technologies and Targets

Cesium and Aluminum Salts of Dodecatungstophosphoric Acid as Eco-Friendly and Efficient Heterogeneous Catalysts in Organic Synthesis: Some Recent Advances

Asymmetric Epoxidations of α,β‐Unsaturated Carbonyl Compounds

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