20826-50-0Relevant academic research and scientific papers
Enantioselective Oxidative Rearrangements with Chiral Hypervalent Iodine Reagents
Brown, Michael,Kumar, Ravi,Rehbein, Julia,Wirth, Thomas
supporting information, p. 4030 - 4035 (2016/03/16)
A stereoselective hypervalent iodine-promoted oxidative rearrangement of 1,1-disubstituted alkenes has been developed. This practically simple protocol provides access to enantioenriched α-arylated ketones without the use of transition metals from readily
Catalytic, oxidant-free, direct olefination of alcohols using Wittig reagents
Khaskin,Milstein
supporting information, p. 9002 - 9005 (2015/05/27)
Reported here is the catalytic, acceptorless coupling of alcohols with in situ generated, non-stabilized phosphonium ylides to form olefins as major products. The reaction uses low catalyst loadings and does not require added oxidants. Hydrogenation of the product is minimized and the reaction leads to Z (aliphatic) or E (benzylic) stereospecificity.
Enantioselective synthesis of all-carbon quaternary stereogenic centers via copper-catalyzed asymmetric allylic alkylation of (Z)-allyl bromides with organolithium reagents
Faans-Mastral, Martn,Vitale, Romina,Prez, Manuel,Feringa, Ben L.
, p. 4209 - 4212 (2015/03/14)
A copper/phosphoramidite catalyzed asymmetric allylic alkylation of Z trisubstituted allyl bromides with organolithium reagents is reported. The reaction affords all-carbon quaternary stereogenic centers in high yields and very good regio- and enantiosele
Capture of in situ generated diazo compounds or copper carbenoids by triphenylphosphine: Selective synthesis of trans-alkenes and unsymmetric azines via reaction of aldehydes with ketone-derived N-tosylhydrazones
Sha, Qiang,Ling, Yifei,Wang, Wenyong,Wei, Yunyang
supporting information, p. 2145 - 2150 (2013/10/01)
Copper(II) acetylacetonate-catalyzed Wittig olefination reactions of aldehydes with ketone-derived N-tosylhydrazones are reported. A series of tosylhydrazones was investigated and our results showed that the carbon number of the alkyl chain influences the E-selecivity of the alkenes greatly. Alkenes could be obtained in moderate yields and excellent E-selectivity when the carbon numbers were up to two. Under metal-free conditions, triphenylphosphine was able to capture the in situ generated diazo compounds and the corresponding unsymmetrical azines were formed in good yields.
Silicon-(thio)urea Lewis acid catalysis
Hrdina, Radim,Mueller, Christian E.,Wende, Raffael C.,Lippert, Katharina M.,Benassi, Mario,Spengler, Bernhard,Schreiner, Peter R.
supporting information; experimental part, p. 7624 - 7627 (2011/06/26)
We present a new class of catalysts based on the combination of N,N′-diaryl(thio)ureas and weak silicon Lewis acids (e.g., SiCl 4). Such silicon-(thio)urea catalysts effectively catalyze the stereospecific rearrangement of epoxides to quaternary carbaldehydes.
Friedel-Crafts alkylation of benzene and toluene with olefinic C6 hydrocarbons and esters
Black, Kenneth D.,Gunstone, Frank D.
, p. 79 - 86 (2007/10/03)
To assist our study of the reaction of toluene and other aromatic compounds with methyl oleate and other olefinic esters, benzene and toluene have been alkylated under Friedel-Crafts conditions with hex-1-ene, hex-3-ene, methyl hex-3-enoate and methyl hex-3-enedioate. The products were isolated and identified by NMR and mass spectrometric procedures.
Palladium-Assisted (Z)-(E) Isomerization of Styrenes
Giles, Robin G. F.,Son, Vanessa R. Lee,Sargent, Melvyn V.
, p. 777 - 781 (2007/10/02)
It is shown that treatment of stereoisomeric mixtures of styrenes with a catalytic amount of bis(acetonitrile)dichloropalladium(II) achieves smooth stereoisomerization of the (Z)-isomers to the (E)-isomers.
