- Diastereoselective synthesis of fused lactone-pyrrolidinones; Application to a formal synthesis of (-)-salinosporamide a
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A mild, diastereoselective synthesis of fused lactone-pyrrolidinones using an oxidative radical cyclization is reported. The methodology is demonstrated in a formal synthesis of (-)-salinosporamide A.
- Logan, Angus W. J.,Sprague, Simon J.,Foster, Robert W.,Marx, Leo B.,Garzya, Vincenzo,Hallside, Michal S.,Thompson, Amber L.,Burton, Jonathan W.
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Read Online
- A simple and non-conventional method for the synthesis of selected β-arylalkylchalcogeno substituted alcohols, amines and carboxylic acids
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A simple and mild procedure for the reaction of nucleophilic chalcogenium species (Se and Te) with lactones, epoxides or aziridines to prepare chalcogen-containing acids, alcohols and amines in non-conventional media is described. The chalcogenolate nucle
- Borges, Elton L.,Jacob, Raquel G.,Lenard?o, Eder J.,Lima, David B.,Perin, Gelson,Silva, Márcio S.,Silva, Patrícia C.
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p. 376 - 389
(2017/02/05)
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- Switchable catalytic activity: Selenium-containing peptides with redox-controllable self-assembly properties
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Mimicking nature: The reversible formation of self-assembled nanostructures of selenium-containing peptides can be controlled by redox triggers (see scheme, VC=vitamin C). As a consequence, the catalytic activity of these peptides is switchable. These res
- Miao, Xiaoming,Cao, Wei,Zheng, Wenting,Wang, Jingyu,Zhang, Xiaoli,Gao, Jie,Yang, Chengbiao,Kong, Deling,Xu, Huaping,Wang, Ling,Yang, Zhimou
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p. 7781 - 7785
(2013/08/23)
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- Nucleophilic ring opening of mono-activated cyclopropanes with arylselenolates generated from diselenides in the presence of a Zn/AlCl 3 system
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An efficient one-pot synthesis of γ-arylselenenyl ketones, acids, and nitriles is presented. The method uses Zn/AlCl3-promoted cleavage of diselenides and subsequent ring-opening of mono-activated cyclopropanes. Georg Thieme Verlag Stuttgart.
- Nazari, Mohammad,Movassagh, Barahman
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experimental part
p. 1803 - 1805
(2009/12/04)
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- Stereospecific synthesis of ss3-amino acid derivatives from propargylic alcohols: Efficient solution-phase synthesis of oligopeptides without coupling agents
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A stereospecific synthesis of ss3-amino acids has been accomplished starting from readily available and enantioenriched propargylic alcohols. This conversion can be effected in only three steps by selenium-mediated organic transformations of th
- Temperini, Andrea,Terlizzi, Raffaella,Testaferri, Lorenzo,Tiecco, Marcello
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supporting information; experimental part
p. 7883 - 7895
(2010/03/24)
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- Nucleophilic cleavage of lactones and esters with zinc selenolates prepared from diselenides in the presence of Zn/AlCl3
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The utility of zinc selenolates for effecting nucleophilic cleavage of simple lactones and esters has been investigated. When zinc selenolate generated via Zn/AlCl3-promoted cleavage of diselenides was reacted with simple lactones and esters, efficient nucleophilic alkyl-oxygen bond cleavage proceeded generating the corresponding carboxylic acids in moderate to excellent yields.
- Nazari, Mohammad,Movassagh, Barahman
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scheme or table
p. 438 - 441
(2009/05/27)
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- Convenient preparation of benzylseleno- and phenylselenoalkanoic acids: Reagents for synthesis of organoselenium compounds
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An efficient and operationally simple route to benzylseleno- and phenylselenoalkanoic acids from ethyl benzyl/phenylselenoalkanoates is described. This involves preparation of ethyl benzyl/phenylselenoalkanoates as substrates by reaction of dibenzyl/diphenyl diselenide and sodium borohydride with ethyl chloroalkanoates in ethanol followed by basic hydrolysis and subsequent acidification. Copyright Taylor & Francis Group, LLC.
- Bhalla, Aman,Sharma, Sitansh,Bhasin, Kuldip K.,Bari, Shamsher S.
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p. 783 - 793
(2007/10/03)
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- Formal α-Vinylation of Amino Acids. Use of a New Benzeneselenolate Equivalent
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A new synthetic approach to the formal α-vinylation of α-amino acids is described, in which the readily available electrophile, ethylene oxide, serves as the vinyl cation equivalent.N-Benzoyl α-amino esters bearing appropriate side-chain protecting groups
- Pedersen, Michelle L.,Berkowitz, David B.
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p. 6965 - 6975
(2007/10/02)
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- A reagent for the efficient cleavage of N-benzoylhomoserine lactones: Access to α-(2-phenylseleno)ethyl amino acids
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Upon heating diphenyl diselenide and sodium trimethoxyborohydride (1:2) in DMF to 60°C, a reagent is produced which efficiently cleaves α-substituted N-benzoylhomoserine lactones to the corresponding α-(2-phenylseleno)ethyl amino acids without competing l
- Pedersen,Berkowitz
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p. 7315 - 7318
(2007/10/02)
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- CONVENIENT PREPARATION OF SODIUM AND POTASSIUM PHENYL SELENIDES. REDUCTION OF THE SELENIUM-SELENIUM BOND BY SODIUM HYDRIDE AND POTASSIUM HYDRIDE.
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Sodium and potassium phenyl selenides are conveniently prepared by brief reflux of diphenyl diselenide with sodium hydride and potassium hydride, respectively.
- Dowd, Paul,Kennedy, Paul
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p. 935 - 942
(2007/10/02)
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- Substitution Reactions of Thallous Thiophenoxide and Thallous Phenylselenide with Halogen-Bearing Substrates
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Thallous thiophenoxide (1) and thallous selenide (2) were prepared by the action of either thallous ethoxide or thallous pentoxide on thiophenol and benzeneselenol.The reagents 1 and 2 reacted readily with aroyl and acyl halides, imidoyl chlorides, α-halo ketones, α-halo esters, α-halo lactones, α-halo carboxylic acids, allyl halides, alkyl halides, chlorotrimethylsilane, chloroacetonitrile, and N-chlorosuccinimide to give substitution products and varying amounts of diphenyl disulfide and diphenyl diselenide.The reactions were run as heterogeneous mixtures in ether.The origin of the diphenyl disulfide and diphenyl diselenide was homolytic cleavage of the thallium-sulfur or thallium-selenium bond, on the basis of the products derived from the reactions of N-chlorosuccinimide with 1 and 2.
- Detty, Michael R.,Wood, Gary P.
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