74796-14-8Relevant academic research and scientific papers
Copper-mediated oxidative transformation of N-allyl enamine carboxylates toward synthesis of azaheterocycles
Toh, Kah Kah,Biswas, Anup,Wang, Yi-Feng,Tan, Yun Yun,Chiba, Shunsuke
supporting information, p. 6011 - 6020 (2014/05/20)
A method for synthesis of 3-azabicyclo[3.1.0]hex-2-enes has been developed by intramolecular cyclopropanation of readily available N-allyl enamine carboxylates. Two complementary reaction conditions, CuBr-mediated aerobic and CuBr2-catalyzed-PhIO2-mediated systems effectively induced stepwise cyclopropanation via carbocupration of alkenes. Oxidative cyclopropane ring-opening of 5-substituted 3-azabicyclo[3.1.0]hex-2-enes was also developed for synthesis of highly substituted pyridines. In addition, diastereoselective reduction of 3-azabicyclo[3.1.0]hex-2-enes to 3-azabicyclo[3.1.0]hexanes was achieved using NaBH3CN in the presence of acetic acid.
Copper-mediated aerobic synthesis of 3-azabicyclo[3.1.0]hex-2-enes and 4-carbonylpyrroles from N-allyl/propargyl enamine carboxylates
Toh, Kah Kah,Wang, Yi-Feng,Ng, Eileen Pei Jian,Chiba, Shunsuke
supporting information; experimental part, p. 13942 - 13945 (2011/10/30)
Synthetic methods for 3-azabicyclo[3.1.0]hex-2-enes and 4-carbonylpyrroles have been developed that use copper-mediated/catalyzed reactions of N-allyl/propargyl enamine carboxylates under an O2 atmosphere and involve intramolecular cyclopropanation and carbooxygenation, respectively. These methodologies take advantage of orthogonal modes of chemical reactivity of readily available N-allyl/propargyl enamine carboxylates; the complementary pathways can be accessed by slight modification of the reaction conditions.
Chiral lewis base catalyzed highly enantioselective reduction of N-alkyl β-enamino esters with trichlorosilane and water
Wu, Xinjun,Li, Yang,Wang, Chao,Zhou, Li,Lu, Xiaoxia,Sun, Jian
supporting information; experimental part, p. 2846 - 2848 (2011/04/24)
First, test the water! In the presence of a chiral Lewis base catalyst 2, the supposedly moisture-unfriendly reduction system with trichlorosilane was found to be highly efficient and enantioselective when using water as an additive. For the first time, this method enables the reduction of a broad range of N-alkyl β-enamino esters 1 to give N-alkyl β-amino esters 3 in good to high yields and with excellent enantioselectivities (see scheme).
Dioxopyrrolines. XXVII. Syntheses of 2-Aryl-3-ethoxycarbonyl-Δ2-pyrroline-4,5-diones
Sano, Takehiro,Horiguchi, Yoshie,Toda, Jun,Imafuku, Kazue,Tsuda, Yoshisuke
, p. 497 - 503 (2007/10/02)
2-Aryl-3-ethoxycarbonyl-Δ2-pyrroline-4,5-diones (3) were easily prepared in good yields by condensation of enamino-esters (2) with oxalyl chloride.The products were characterized by ultraviolet and infrared spectroscopy. Keywords - Δ2-pyrroline-4,5-dione; dioxopyrroline; enamino-ester; ethyl 3-aryl-3-aminopropenoate; 2-aryl-3-ethoxycarbonyl-Δ2-pyrroline-4,5-dione; UV; restricted rotation
