4638-79-3Relevant academic research and scientific papers
Synthesis of trans-2-Substituted Cyclopropylamines from α-Chloroaldehydes
West, Michael S.,Mills, L. Reginald,McDonald, Tyler R.,Lee, Jessica B.,Ensan, Deeba,Rousseaux, Sophie A. L.
supporting information, p. 8409 - 8413 (2019/10/14)
Cyclopropylamines are prevalent in pharmaceuticals and agrochemicals. Herein, we report the synthesis of trans-2-substituted cyclopropylamines in high diastereoselectivity from readily available α-chloroaldehydes. The reaction proceeds via trapping of an electrophilic zinc homoenolate with an amine followed by ring closure to generate the cyclopropylamine. We have also observed that cyclopropylamine cis/trans-isomerization occurs in the presence of zinc halide salts and that this process can be turned off by the addition of a polar aprotic cosolvent.
Carbene-Catalyzed α-Carbon Amination of Chloroaldehydes for Enantioselective Access to Dihydroquinoxaline Derivatives
Huang, Ruoyan,Chen, Xingkuan,Mou, Chengli,Luo, Guoyong,Li, Yongjia,Li, Xiangyang,Xue, Wei,Jin, Zhichao,Chi, Yonggui Robin
, p. 4340 - 4344 (2019/06/14)
An NHC-catalyzed α-carbon amination of chloroaldehydes was developed. Cyclohexadiene-1,2-diimines are used as amination reagents and four-atom synthons. Our reaction affords optically enriched dihydroquinoxalines that are core structures in natural products and synthetic bioactive molecules.
Cascade Trisulfur Radical Anion (S3?-) Addition/Electron Detosylation Process for the Synthesis of 1,2,3-Thiadiazoles and Isothiazoles
Liu, Bei-Bei,Bai, Hui-Wen,Liu, Huan,Wang, Shun-Yi,Ji, Shun-Jun
, p. 10281 - 10288 (2018/07/25)
Trisulfur radical anion (S3?-) mediated reactions with in situ formed azoalkenes and α,β-usaturated N-sulfonylimines for the construction of 1,2,3-thiadiazoles and isothiazoles has been developed. S3?- is in situ generated from potassium sulfide in DMF. These two approaches provide a new, safe, and simple way to construct 4-subsituted 1,2,3-thiadiazoles, 5-subsituted 1,2,3-thiadiazoles, and isothiazole in good yields. The reactions include the formation of the new C-S and N-S bonds via S3?- addition and electron detosylation under mild conditions.
Carbene and Acid Cooperative Catalytic Reactions of Aldehydes and o-Hydroxybenzhydryl Amines for Highly Enantioselective Access to Dihydrocoumarins
Chen, Xingkuan,Song, Runjiang,Liu, Yingguo,Ooi, Chong Yih,Jin, Zhichao,Zhu, Tingshun,Wang, Hongling,Hao, Lin,Chi, Yonggui Robin
supporting information, p. 5892 - 5895 (2017/11/10)
A highly enantioselective method for quick access to dihydrocoumarins is reported. The reaction involves a cooperative catalytic process with carbene and in situ generated Br?nsted acid as the catalysts. α-Chloro aldehyde and readily available and stable
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.
An organocascade approach to α,α-chlorofluoroalcohols
Hayes, Montgomery D.,Rodríguez-Alvarado, Melanie,Brenner-Moyer, Stacey E.
supporting information, p. 4718 - 4720 (2015/08/06)
Abstract Fluorinated, tetrasubstituted, carbon stereocenters are challenging to install enantioselectively. gem-Chlorofluoro compounds contain a fluorinated, tetrasubstituted stereocenter, and are an entrée into other such compounds. We report herein the first catalytic, enantioselective method to prepare gem-chlorofluoro compounds from unfunctionalized aldehydes. This one-pot method precludes the isolation of volatile and/or reactive α-haloaldehyde intermediates.
Synthesis of 3-arylcoumarins through N-heterocyclic carbene catalyzed condensation and annulation of 2-chloro-2-arylacetaldehydes with salicylaldehydes
Jiang, Yuansong,Chen, Wanzhi,Lu, Weimin
, p. 3669 - 3676 (2013/05/08)
The condensation reaction of 2-chloro-2-arylacetaldehyde with salicylaldehyde catalyzed by N-heterocyclic carbene (NHC) leading to 3-arylcoumarin was studied. A number of 3-arylcoumarin derivatives were obtained in good to excellent yields via this umpolung reaction. This reaction is facile and experimentally simple and mild.
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.
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
