84782-51-4Relevant articles and documents
K2S2O8-promoted C-Se bond formation to construct α-phenylseleno carbonyl compounds and α,β-unsaturated carbonyl compounds
Yang, Xue-Yan,Wang, Ruizhe,Wang, Lu,Li, Jianjun,Mao, Shuai,Zhang, San-Qi,Chen, Nanzheng
, p. 28902 - 28905 (2020/08/25)
A novel K2S2O8-promoted C-Se bond formation from cross-coupling under neutral conditions has been developed. A variety of aldehydes and ketones react well using K2S2O8 as the oxidant in the absence of catalyst and afford desired products in moderate to excellent yields. This protocol provides a very simple route for the synthesis of α-phenylseleno carbonyl compounds and α,β-unsaturated carbonyl compounds.
KF/Al2O3 and PEG-400 as a recyclable medium for the selective α-selenation of aldehydes and ketones. Preparation of potential antimicrobial agents
Victoria, Francine Novack,Radatz, Cátia S.,Sachini, Maraisa,Jacob, Raquel G.,Perin, Gelson,da Silva, Wladimir P.,Lenard?o, Eder J.
experimental part, p. 6761 - 6763 (2010/04/27)
2-Phenylseleno aldehydes and ketones were selectively obtained using solid-supported catalyst (KF/Al2O3) and PEG-400 as clean, recyclable medium in good to excellent yields. The method was applied in the preparation of highly functio
ORGANOCATALYSTS AND METHODS OF USE IN CHEMICAL SYNTHESIS
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Page/Page column 52-53; 97-98, (2010/02/15)
The present invention pertains generally to compositions comprising organocatalysts that facilitate stereo-selective reactions and the method of their synthesis and use. Particularly, the invention relates to metal-free organocatalysts for facilitation of stereo--selective reactions, and the method of their synthesis and use. These compounds have the structure of the Formulas (I) and (II). Where X is independently selected from CH2, N-Ra, O, S or C=O; Y is CH2, N-Ra, O, S or C=O, with the proviso that at least one of X or Y is CH2, and preferably both of X and Y are CH2; Ra is H, an optionally substituted C1-C12 alkyl, preferably an optionally substituted C1-C6alkyl including a C3-C6 cyclic alkyl group, or an optionally substituted aryl group, preferably an optionally substituted phenyl group; Rb is H, an optionally substituted C1-C12 alkyl, preferably an optionally substituted C1-C6 acyclic or a a C3-C6 cyclic alkyl group, CHO, N(Me)O, CO(S)Ra or the group of Formula (III). Where Rc and Rd are each independently H, F, C1, an optionally substituted C1-C20 alkyl, preferably an optionally substituted C1-C12 alkyl, more preferably a C1-C6 alkyl, and an optionally substituted aryl group, or together Rc and Rd form an optionally substituted carbocyclic or optionally substituted heterocyclic ring; R1 is OH, OR, NR'R", NHC(=O)R, NHSO2R; R2 is H, F, C1, an optionally substituted C1-C20 alkyl, preferably an optionally substituted C1-C6 alkyl, an optionally substituted aryl group or a =O group (which establishes a carbonyl group with the carbon to which =O is attached; R3 is H, OH, F, C1, Br, I, Cl, an optionally substituted C1-C20 alkyl, alkenyl or alkynyl ("hydrocarbyl") group, preferably an optionally substituted C1-C6 alkyl, or an optionally substituted aryl, such that the carbon to which R3 is attached has an R or S configuration; R is H, an optionally substituted C1-C20 alkyl, preferably an optionally substituted C1-C6 alkyl, or an optionally substituted aryl group, R' and R" are each independently H, an optionally substituted C1-C20 alkyl group, preferably an optionally substituted C1-C6 alkyl, or an optionally substituted aryl group; or together R' and R" form an optionally substituted heterocyclic, preferably a 4 to 7 membered optionally substituted heterocyclic group or an optionally substituted heteroaryl ring with the nitrogen to which R' and R" are attached; and wherein said compound is free from a metal catalyst.
Direct, facile aldehyde and ketone α-selenenylation reactions promoted by L-prolinamide and pyrrolidine sulfonamide organocatalysts
Wang, Jian,Li, Hao,Mei, Yujiang,Lou, Bihshow,Xu, Dingguo,Xie, Daiqian,Guo, Hua,Wang, Wei
, p. 5678 - 5687 (2007/10/03)
A new catalytic method for direct α-selenenylation reactions of aldehydes and ketones has been developed. The results of exploratory studies have demonstrated that L-prolinamide is an effective catalyst for α-selenenylation reactions of aldehydes, whereas
A simple and efficient L-prolinamide-catalyzed α-selenenylation reaction of aldehydes
Wang, Wei,Wang, Jian,Li, Hao
, p. 2817 - 2820 (2007/10/03)
An efficient and simple L-prolinamide-catalyzed α-selenenylation reaction of aldehydes with N-(phenylseleno)phthalimide has been developed for the efficient preparation of a-phenylselenoaldehydes. Such compounds are versatile building blocks for the synth
A novel approach to chiral, nonracemic pyrrolidines by 5-exo-trig diastereoselective radical cyclization on acrylamides derived from (-)-8- aminomenthol
Andres, Celia,Duque-Soladana, Juan P.,Pedrosa, Rafael
, p. 4282 - 4288 (2007/10/03)
α,β-Unsaturated amides supported on perhydro-1,3-benzoxazines derived from (-)-8-aminomenthol as chiral auxiliaries undergo regio- and stereoselective 5-exo-trig radical cyclization leading to diastereomeric five-membered lactams. These cyclization products are transformed into enantiopure 3,4-disubstituted pyrrolidines by reduction with aluminum hydride followed by removal of the menthol appendage.
Use of phenylselenium trichloride for simple and rapid preparation of α-phenylselanyl aldehydes and ketones
Houllemare, Didier,Ponthieux, Sylvain,Outurquin, Francis,Paulmier, Claude
, p. 101 - 106 (2007/10/03)
α-Phenylselanyl aldehydes are prepared on a large scale by reaction of PhSeCl3 with the corresponding aldehydes in acetonitrile without isolation of the intermediate dichloro adducts. This method has been applied to α-phenylselanyl ketones deri
ORGANOSELENIUM COMPOUNDS. VIII. SYNTHESIS OF α-(ARYLSELENO)PROPIONALDEHYDES
Nedugov, A. N.,Pavlova, N. N.,Shalimov, A. V.
, p. 226 - 228 (2007/10/02)
The reaction of arylselenomagnesium bromides with propargyl alcohol in diethyl ether leads at the first stage to the formation of β-(arylseleno)allyl alcohols, the acid hydrolysis of which gives α-(arylseleno)propionaldehydes.
Allylic Selenides in Organic Synthesis: New Methods for the Synthesis of Allylic Amines
Shea, Regan G.,Fitzner, Jeffrey N.,Fankhauser, John E.,Spaltenstein, Andreas,Carpino, Philip A.,et al.
, p. 5243 - 5252 (2007/10/02)
Oxidative rearrangement of allylic selenides in the presence of various amine nucleophiles provides synthetic access to a variety of allylic amine derivatives.The stereochemical outcome of these reactions has been investigated, and is consistent with a -sigmatropic rearrangement mechanism.Several D-α-amino acids and racemic β,γ-unsaturated α-amino acids were prepared in this manner.A variant of this process employing an achiral allylic selenide and chiral amide afforded protected allylic amines in low diastereoisomeric excess.
Preparations de composes α-arylselenocarbonyles a l'aide de morpholinoareneselenenamides
Lerouge, Patrice,Paulmier, Claude
, p. 1219 - 1224 (2007/10/02)
The reactivity of the morpholinoareneselenenamides 1 which are readily prepared from various diaryldiselenides, is investigated.The selenenamides 1 are good α-selenenylating agents for aliphatic aldehydes, α-ketoesters and conjugated enals yielding the α-
