676272-23-4Relevant academic research and scientific papers
Direct Cyclopropanation of α-Cyano β-Aryl Alkanes by Light-Mediated Single Electron Transfer Between Donor–Acceptor Pairs
Li, Jing,Lear, Martin J.,Hayashi, Yujiro
supporting information, p. 5901 - 5905 (2021/03/09)
Cyclopropanes are traditionally prepared by the formal [2+1] addition of carbene or radical based C1 units to alkenes. In contrast, the one-pot intermolecular cyclopropanation of alkanes by redox active C1 units has remained unrealised. Herein, we achieve
Diastereoselective Synthesis of Spiro[2.3]hexanes from Methylenecyclopropane and Cyanoalkenes Catalyzed by a Tin-Ate Complex
Suzuki, Itaru,Shimazu, Jun-ya,Tsunoi, Shinji,Shibata, Ikuya
supporting information, p. 3658 - 3661 (2019/06/17)
A diastereoselective synthesis of spiro[2.3]hexane catalyzed by Sn and Mg halides was developed from a combination of methylenecyclopropane and cyanoalkene bearing an ester group. The selectivity was affected by the size of the halogen in the catalyst and
Chemoselective phosphine-catalyzed cascade annulations between two different activated alkenes: Highly diastereoselective syntheses of polysubstituted cyclohexanes and cyclopentenes
Cai, Lingchao,Zhang, Bo,Wu, Guiping,Song, Haibin,He, Zhengjie
supporting information; experimental part, p. 1045 - 1047 (2011/02/26)
Chemoselective phosphine-catalyzed cascade [2 + 2 + 2] and [2 + 2 + 1] annulations between two molecules of 2-arylmethylidene cyanoacetates or malononitriles and one molecule of α,β-unsaturated ketones have been developed. Under the nucleophilic catalysis
An efficient synthetic route for pyrrolizinone synthesis through functionalized c-alkylpyrroles
Unaleroglu, Canan,Tasgin, Dilek Isik,Aytac, Sertan,Temelli, Baris
body text, p. 3243 - 3250 (2010/02/27)
Regioselective addition of pyrrole to methyl 3-aryl-2-cyanoacrylates was achieved, in high yields, with copper(II) triflate as the catalyst in toluene. C-Alkylated pyrroles afforded novel pyrrolizin-3-ones, in good to high yields and high diastereomeric r
Superacid-catalyzed intramolecular cyclization reaction of arylcyanopropionate: Geminal substitution effect on superelectrophilicity
Nakamura, Satoshi,Sugimoto, Hiromichi,Ohwada, Tomohiko
, p. 4219 - 4224 (2008/09/20)
(Chemical Equation Presented) We present superacid-catalyzed intramolecular cyclization reactions of arylcyanopropionates to give cyclized five- and six-membered β-enamino esters in moderate to high yields. Known intramolecular ring-closing reactions of protonated nitrile to aromatic carbon atom are limited to the 6-membered case. Interestingly, a significant synergistic increase of reactivity of the cyano functionality was observed, and the cyano nitrogen atom was converted into an amino group, when an ester group was present in a geminal arrangement. Deuterium exchange experiments excluded the involvement of deprotonation of the α-proton in the cyclization process. The acidity dependence of the cyclization reactions and 13C NMR studies of a model compound, methyl cyanoacetate, in various acidic media were consistent with the involvement of the O,N-diprotonated dication of methyl cyanoacetate, a distonic dication, in strong acid, and this is considered to be the de facto electrophile in the present cyclization reaction of arylcyanopropionates.
