71666-56-3Relevant academic research and scientific papers
Intramolecular Schmidt Reaction of Vinyl Azides with Cyclic Ketones
Chen, Peng,Sun, Chu-Han,Wang, Yu,Xue, Ying,Chen, Chen,Shen, Mei-Hua,Xu, Hua-Dong
supporting information, p. 1643 - 1646 (2018/03/23)
Cyclic ketones tethered with a vinyl azide group undergo a Schmidt-hydrolysis sequence to give secondary lactams bearing a ketone side chain. Secondary lactams are obtained in a regioselective manner that is not possible in a conventional Schimdt reaction. In addition to the well-documented C-2 nucleophilicity, the N nucleophilicity of vinyl azide disclosed in this work opens a new direction for reaction invention involving vinyl azides.
Intermolecular mono-and dihydroamination of activated alkenes using a recoverable gold catalyst
Medina, Florian,Michon, Christophe,Agbossou-Niedercorn, Francine
supporting information, p. 6218 - 6227 (2013/01/15)
A combination of gold chloride organometallic complex and a silver salt was used to catalyze intermolecular hydroamination of activated alkenes, i.e aza-Michael reactions. The gold-catalyzed reactions of activated alkenes with nitrogen substrates were investigated and found to afford various mono-and dihydroamination products, the latter being rare and original. After flash chromatography, gold NHC catalyst could be recovered as a gold hydroxide NHC complex. When combined with a silver salt, the gold complex lead again to an active hydroamination catalyst.
An unexpected oxidation of unactivated methylene C-H using DIB/TBHP protocol
Zhao, Yi,Yim, Wai-Leung,Tan, Chong Kiat,Yeung, Ying-Yeung
supporting information; experimental part, p. 4308 - 4311 (2011/10/08)
An in situ generated hypervalent iodine species, bis(tert-butylperoxy) iodobenzene, was used as a peroxy radical source for the oxidation of unreactive, remote, and isolated alkyl (cyclic or aliphatic) esters and amides to the corresponding keto compounds under very mild conditions.
Asymmetric reductions of ethyl 2-(benzamidomethyl)-3-oxobutanoate by yeasts
Gandolfi, Raffaella,Cesarotti, Edoardo,Molinari, Francesco,Romano, Diego,Rimoldi, Isabella
scheme or table, p. 411 - 414 (2009/09/08)
The stereoselective reduction of ethyl 2-(benzamidomethyl)-3-oxobutanoate 1 using yeasts was investigated among a restricted number (12) of yeasts. Kluyveromyces marxianus var. lactis CL69 diastereoselectively produced (2R,3S)-ethyl 2-(benzamidomethyl)-3-hydroxybutanoate 2, whereas Pichia glucozyma CBS 5766 gave (2S,3S)-2 as the major stereoisomer. The biotransformations were independently optimized for minimizing by-product formation and maximizing the diastereoselectivity. Under optimized conditions, K. marxianus var. lactis CL 69 gave the (2R,3S)-ethyl 2-(benzamidomethyl)-3-hydroxybutanoate 2 with ee > 99% and de = 98%, while P. glucozyma CBS 5766 allowed for the production of (2S,3S)-2 with ee > 99% and de = 86%.
Generalization of the Benzotriazole-Mediated Introduction of N-Substituents into Amides
Katritzky, Alan R.,Ignatchenko, Alexey V.,Lang, Hengyuan
, p. 4002 - 4005 (2007/10/02)
N-(Benzotriazol-1-ylmethyl) amides 2, easily available by condensation of BtCH2OH with amides, are used for the preparation of a variety of N-substituted amides such as the homoallyl, 1,3-butadienyl, and 2,2-diphenylcyclopropyl derivatives by displacement
