121569-35-5Relevant articles and documents
Investigation of the Organocatalytic Chlorination of 2-Phenylpropanal
Mohr, Lisa-Marie,McCulley, Christina H.,Blom, Jakob,Lamhauge, Johannes N.,Anker J?rgensen, Karl
supporting information, p. 17465 - 17475 (2021/10/25)
Results of an examination of the organocatalytic enantioselective α-chlorination of 2-phenylpropanal are described. Synthetic investigation including the screening of primary and secondary aminocatalysts, many different reaction conditions, and other α-br
Trichloromethanesulfonyl chloride: A chlorinating reagent for aldehydes
Jimeno, Ciril,Cao, Lidong,Renaud, Philippe
, p. 1251 - 1255 (2016/02/19)
Trichloromethanesulfonyl chloride (CCl3SO2Cl), a commercially available reagent, has been found to perform efficiently in the α-chlorination of aldehydes, including its catalytic asymmetric version, under very mild reaction conditions. Under our reaction conditions, this compound outperforms typical chlorinating reagents for organic synthesis, facilitates workup and purification of the product, and minimizes the formation of toxic, chlorinated organic waste.
A simple primary amine catalyst for enantioselective α-hydroxylations and α-fluorinations of branched aldehydes
Witten, Michael R.,Jacobsen, Eric N.
supporting information, p. 2772 - 2775 (2015/06/16)
A new primary amine catalyst for the asymmetric α-hydroxylation and α-fluorination of α-branched aldehydes is described. The products of the title transformations are generated in excellent yields with high enantioselectivities. Both processes can be performed within short reaction times and on gram scale. The similarity in results obtained in both reactions, combined with computational evidence, implies a common basis for stereoinduction and the possibility of a general catalytic mechanism for α-functionalizations. Promising initial results in α-amination and α-chlorination reactions support this hypothesis.
The Rabe amination after a century: Direct addition of N-heterocycles to carbonyl compounds
Scarpino Schietroma, Daniele M.,Monaco, Mattia R.,Bucalossi, Valerio,Walter, Philipp E.,Gentili, Patrizia,Bella, Marco
scheme or table, p. 4692 - 4695 (2012/08/08)
A catalytic version of the Rabe electrophilic amination is presented. This kind of reaction was originally employed in 1918 in a key step for the conversion of quinotoxine to quinine. Ketones and α-substituted aldehydes give the corresponding α-aminated carbonyl compounds in moderate yield. α,α-Unsubstituted aldehydes give rise to amino ketones via a novel rearrangement.
Synthesis of 1,1-bisphosphono-2-aza-1,3-dienes, a new class of electron-deficient azadienes
Masschelein, Kurt G.R.,Stevens, Christian V.
, p. 4336 - 4338 (2008/09/21)
1,1-Bisphosphono-2-aza-1,3-dienes are formed by 1,4-dehydrohalogenation of the corresponding N-(bisphosphonomethyl)-α-haloimines in moderate to good yields. The precursors could be formed by condensation of bisphosphono-amines and the corresponding α-haloaldehydes.
CATALYTIC ASYMMETRIC SYNTHESIS OF OPTICALLY ACTIVE α-HALO-CARBONYL COMPOUNDS
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Page/Page column 17, (2010/02/13)
A process for the catalytic asymmetric synthesis of an optically active compound of the formula (la) or (lb): wherein R is an organic group; X is halogen; Rland R2which may the same or different represents H, or an organic group or R
Stereospecific Construction of Chiral Quaternary α-Oxygenated Aldehydes from Chiral Secondary Alcohol Derivatives
Arasaki, Hideki,Iwata, Masashi,Nishimura, Daisuke,Itoh, Akichika,Masaki, Yukio
, p. 546 - 548 (2007/10/03)
Chiral tertiary dichloromethylcarbinol derivatives 2, prepared from protected chiral secondary alcohols 1, were converted stereospecifically into chiral quaternary α-oxygenated aldehyde derivatives 4 and 11 via intermediary α-chloroepoxides 3 under weakly
Stereospecific construction of chiral quaternary carbon compounds from chiral secondary alcohol derivatives
Masaki, Yukio,Arasaki, Hideki,Iwata, Masashi
, p. 4 - 5 (2007/10/03)
Chiral tertiary dichloromethylcarbinol derivatives, prepared by stereospecific α C-H insertion reaction of dichlorocarbene with protected chiral secondary alcohols, were converted into intermediary α-chloroepoxides which gave stereospecifically chiral qua
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
