23477-91-0Relevant articles and documents
A Change from Kinetic to Thermodynamic Control Enables trans-Selective Stereochemical Editing of Vicinal Diols
Gu, Xin,Wendlandt, Alison E.,Zhang, Yu-An
supporting information, p. 599 - 605 (2022/01/03)
Here, we report the selective, catalytic isomerization of cis-1,2-diols to trans-diequatorial-1,2-diols. The method employs triphenylsilanethiol (Ph3SiSH) as a catalyst and proceeds under mild conditions in the presence of a photoredox catalyst and under
Stereoselective hydrogenation of methylcyclohex-2-ene-1,4-diols used in the synthesis of ampelomins and deoxy-carbasugars
Lagreca, María Eugenia,Carrera, Ignacio,Seoane, Gustavo A.,Brovetto, Margarita
, p. 853 - 856 (2014/02/14)
Stereoselective hydrogenation of methylcyclohex-2-ene-1,4-diols used as important intermediates for the preparation of ampelomins and deoxy-carbasugars was studied. These olefins were obtained in few steps from a chiral cis-diol resulting from microbial o
Acid-catalyzed aldol-Meerwein-Ponndorf-Verley-etherification reactions - Access to defined configured quaternary stereogenic centers
Seifert, Andrea,Rohr, Kerstin,Mahrwald, Rainer
scheme or table, p. 1137 - 1144 (2012/02/15)
A novel asymmetric aldol-reduction-etherification process of aliphatic enolizable aldehydes is described. The intermediately formed aldol adducts - β-hydroxyaldehydes - were reduced and transformed into the corresponding 1,3-diol ethers by external secondary alcohols at the same time. Thus, with the help of chiral secondary alcohols an access to optically active 1,3-diol ether is given. Furthermore, asymmetric cross-aldol-Meerwein-Ponndorf reactions of enolizable aldehydes can also be realized under these reaction conditions.
Asymmetric acid-catalyzed meerwein-ponndorf-verley-aldol reactions of enolizable aldehydes
Seifert, Andrea,Scheffler, Ulf,Markert, Morris,Mahrwald, Rainer
supporting information; experimental part, p. 1660 - 1663 (2010/09/05)
A highly, stereo- and regioselective Meerwein-Ponndorf-Verley-Aldol etherification process of enolizable aldehydes is described. This new transformation is catalyzed by trifluoroacetic acid. The method also allows cross-aldol reactions with α-branched enolizable aldehydes and thus provides access to defined configured quaternary stereogenic centers.
Synthesis and examination of antimicrobial properties of aminomethylated derivatives C6-C7 of alicyclic diols
Alimardanov,Sadygov,Suleimanova,Dzhafarova,Abdullaeva,Babaev
scheme or table, p. 1255 - 1262 (2009/12/08)
Synthesis of C6-C7 alicyclic diols was studied by a catalytic oxidation of cyclohexene, norbornene and their methyl derivatives in the presence of heterogenized molybdenum-containing catalysts. By a triple condensation of the diols with formaldehyde and secondary amines a synthesis of their aminomethylated derivatives with various substituents at nitrogen atom was examined. Antimicrobial properties of the synthesized amino alcohols in M-10 oil as additives with fungicidal and bactericidal activities were studied.
The Regiochemistry and Stereochemistry of the Hydroboration of Allylsilanes
Fleming, Ian,Lawrence, Nicholas J.
, p. 3309 - 3326 (2007/10/02)
The hydroboration of a wide range of allylsilanes 3 and 5-21 is found to be generally regioselective for attachment of the boron to C-3 and hydrogen to C-2 of the allyl unit, and to be generally stereoselective in the sense 1, with attachment of the boron
The Use of Bismuth(III) Acetate in 'Wet' and 'Dry' Prevost Reactions
Trainor, Robert W.,Deacon, Glen B.,Jackson, W. Roy,Giunta, Nunzio
, p. 1265 - 1280 (2007/10/02)
cis-Diol and trans-diol derivatives can be prepared from alkenes by reaction with iodine and bismuth(III) acetate in 'wet' and 'dry' acetic acid, respectively.Reactions using lesser amounts of bismuth(III) acetate under 'dry' conditions give iodo acetates and under 'wet' conditions a mixture of iodohydrins and iodo ethers.Comparison of these reactions with those promoted by silver, copper, mercury and thallium salts is included.
Intermediates for preparing optically active carboxylic acids
-
, (2008/06/13)
A process is described for preparing optically active alpha-arylalkanoic acids consisting of rearranging an optically active ketal of formula STR1 in which the substituents have the meaning given in the description of the invention.
Asymmetric Dihyroxylation of Alkenes with Osmium Tetroxide: Chiral N,N'-Dialkyl-2,2'-bipyrrolidine Complex
Hirama, Masahiro,Oishi, Tohru,Ito, Sho
, p. 665 - 666 (2007/10/02)
Asymmetric osmylation of alkenes by using N,N'-dialkyl-2,2'-bipyrrolidines as the chiral ligands shows a high asymmetric induction and a marked dependence of the enantioselectivity on both the N-alkyl group and the reaction solvent.
Saturated analogues of poison ivy allergens. Synthesis of trans,trans- and cis,trans-3-alkyl-1,2-cyclohexanediols and sensitizing properties in allergic contact dermatitis
Lepoittevin,Benezra
, p. 287 - 291 (2007/10/02)
Saturated analogues of poison ivy and oak allergens (3-alkylcatechols), i.e. trans,trans-3-alkyl-1,2-cyclohexanediols (alkyl = CH3, n-C5H11, n-C10H21, n-C15H31), have been prepared and used to sensitize guinea pigs. Only long-chain derivatives (carbon chain length > C10) are contact sensitizers. The sensitized animals cross-react to PDC (i.e. pentadecylcatechol, one of the allergens of poison ivy), but the converse is not true (PDC-sensitized animals do not react to cyclohexanediols). cis,trans-3-n-Pentadecyl-1,2-cyclohexanediol has also been synthesized and shown to be a sensitizer. There is not cross-reaction between trans,trans- and cis,trans-3-n-pentadecylcyclohexanediols, excluding a common skin metabolite.
