473723-63-6Relevant academic research and scientific papers
Asymmetric synthesis of chiral glutaric acid derivatives via Rh-catalyzed enantioselective hydrogenation
Duan, Zheng-Chao,Hu, Xiang-Ping,Deng, Jun,Yu, Sai-Bo,Wang, Dao-Yong,Zheng, Zhuo
, p. 588 - 592 (2009)
The first Rh-catalyzed enantioselective hydrogenation of dimethyl 2-methyleneglutarate and its derivatives has been reported. For the hydrogenation of dimethyl 2-methyleneglutarate with a chiral ferrocene-based monodentate phosphoramidite ligand (FAPhos), good enantioselectivity (over 90% ee) with full conversions was achieved. In contrast, the hydrogenation of substrates bearing an aryl substituent at a methylene moiety proved to be more difficult, in which the best enantioselectivity of up to 81% ee was obtained by the use of a P-stereogenic BoPhoz-type ligand.
N-bromosuccinimide-mediated radical cyclization of 3-arylallyl azides: Synthesis of 3-substituted quinolines
Wang, Wei-Xia,Zhang, Qing-Zhao,Zhang, Tian-Qi,Li, Zhan-Shan,Zhang, Wei,Yu, Wei
supporting information, p. 221 - 226 (2015/02/19)
Visible light irradiation of N-bromosuccinimide serves as an effective means to convert methyl 2-(azidomethyl)-3-arylpropenoates and 2-(azidomethyl)-3-arylacrylonitriles to the corresponding iminyl radicals via ?±-hydrogen abstraction and subsequent extrusion of dinitrogen. Thus formed iminyl radicals then undergo intramolecular ortho attack on the aryl ring, affording methyl quin-oline-3-carboxylates and quinoline-3-carbonitriles respectively.
Pd-catalyzed decarboxylative allylic coupling of acetates of Baylis-Hillman alcohols with propiolic acids: A highly regio- and stereoselective synthesis of 1,5-diarylpent-1-en-4-yne derivatives
Tummanapalli, Satyanarayana,Muthuraman, Parthasarathy,Vangapandu, Dhanunjaya Naidu,Shanmugavel, Gnanakalai,Kambampati, Sanjeeva,Lee, Kee Wei
, p. 49392 - 49399 (2015/06/16)
Pd-catalyzed decarboxylative allylic coupling of acetates of Baylis-Hillman alcohols with alkynyl carboxylic acids leading to the formation of an important class of 1,5-diarylpent-1-en-4-ynes in a highly regio- and stereoselective manner has been develope
A general approach to the synthesis of β2-amino acid derivatives via highly efficient catalytic asymmetric hydrogenation of α-aminomethylacrylates
Guo, Yujuan,Shao, Guang,Li, Lanning,Wu, Wenhao,Li, Ruihong,Li, Jingjing,Song, Jian,Qiu, Liqin,Prashad, Mahavir,Kwong, Fuk Yee
experimental part, p. 1539 - 1553 (2010/08/22)
A new strategy was developed for the synthesis of a valuable class of α-aminomethylacrylates via the Baylis-Hillman reaction of different aldehydes with methyl acrylate followed by acetylation of the resulting allylic alcohols and SN2′-type amination of the allylic acetates. Asymmetric hydrogenation of these diverse olefinic precursors using rhodium(Et-Duphos) catalysts provided the corresponding β2-amino acid derivatives with excellent enantioselectivities and exceedingly high reactivities (up to >99.5% ee and S/C=10,000). The first hydrogenation of (Z)-configurated substrates was studied for the synthesis of β2-amino acid derivatives. The high influence of the substrate geometry and steric hindrance on the reactivity and enantioselectivity was also disclosed for this reaction. This protocol provides a highly practical, facile and scalable method for the preparation of optically pure β2- amino acids and their derivatives under mild reaction conditions.
Synthesis of 1,4-oxazepin-7-ones using baylis-hillman products as key intermediates
Nilov, Dmitry,Raecker, Reinhard,Reiser, Oliver
, p. 2232 - 2242 (2007/10/03)
Baylis-Hilman adducts derived from aromatic aldehydes and methyl acrylate can be readily converted to 1,4-oxazepin-7-ones substituted in 2-, 3-, or 4-position by condensation with amino alcohols.
