111836-35-2Relevant academic research and scientific papers
Enantioselective Copper-Catalyzed Electrophilic Sulfenylation of Cyclic Imino Esters
Chen, Zhiwei,Lin, Huaxin,Han, Jian,Fang, Dongmei,Wang, Min,Liao, Jian
supporting information, p. 9146 - 9150 (2021/11/30)
Herein we report an enantioselective sulfenylation of cyclic imino esters with the efficient and versatile sulfenylation reagent S-alkyl 4-methylbenzenesulfonothioates. By utilizing the Cu/tBu-Phosferrox catalytic system, we can assemble diverse S-alkyl groups into the cyclic imino esters under mild conditions in good yields and with excellent enantioselectivities. Remarkably, this method demonstrates a high tolerance of diverse functional groups and proves to be applicable in the late-stage functionalization of pharmaceuticals.
Stereoselective Allylic Alkylation of 1-Pyrroline-5-carboxylic Esters via a Pd/Cu Dual Catalysis
Liu, Penglin,Huo, Xiaohong,Li, Bowen,He, Rui,Zhang, Jiacheng,Wang, Tianhong,Xie, Fang,Zhang, Wanbin
supporting information, p. 6564 - 6568 (2018/10/20)
The asymmetric allylation of 1-pyrroline-5-carboxylic esters has been accomplished through a synergistic Pd/Cu catalyst system under mild reaction conditions. The mechanistic studies suggested that (1) nucleophilic attack is the enantiodiscriminating step; (2) the cooperative action of two chiral reactive species, N-metalated azomethine ylides and ?€-allylpalladium, is most likely responsible for its high reactivity and excellent enantioselectivity (up to >99% ee); and (3) the steric hindrance and electronic factors of the allylic electrophiles and imino ester substrates are crucial for the formation of the linear products. A series of 3,4-2H-pyrrole derivatives bearing a quaternary stereogenic center were easily synthesized in high yields and with high to excellent regioselectivity and enantioselectivity.
Gold-Catalyzed Cycloisomerization of Alkyne-Containing Amino Acids: Controlled Tuning of C–N vs. C–O Reactivity
Medran, Noelia S.,Villalba, Matías,Mata, Ernesto G.,Testero, Sebastián A.
, p. 3757 - 3764 (2016/08/16)
Versatile alkyne-containing amino acids were used as ambident precursors in the divergent synthesis of alkylidenelactones and 1-pyrrolines. Two gold-catalyzed protocols were applied for selective intramolecular O- and N-cycloisomerization reactions.
Novel intramolecular reactivity of oximes: Synthesis of cyclic and spiro-fused imines
Savarin, Cecile G.,Grise, Christiane,Murry, Jerry A.,Reamer, Robert A.,Hughes, David L.
, p. 981 - 983 (2007/10/03)
(Chemical Equation Presented) Under conventional heat (135-145°C) or microwave irradiation and 1 equiv of acetic anhydride, ortho-substituted aryl-oximes undergo a novel sp3 C-H activated cyclization to produce the corresponding isoindoles, and
Double diastereoselectivite de la cycloaddition dipolaire-1,3 d'ylures d'azomethine cycliques substitues
Lakhlifi, Tahar,Sedqui, Ahmed,Fathi, Toufik,Laude, Bernard,Robert, Jean-Francois
, p. 1417 - 1423 (2007/10/02)
Seven derivatives of methyl 5-phenyl-3,4-dihydro-2H-pyrrole-2-carboxylates 1 were synthesized.These compounds are precursors of pentagonal cyclic azomethine ylides, the two sides of which are diastereotopic.The 1,3-dipolar species react with N-methyl and
SYNTHESIS OF α-ACTIVATED Δ1 PYRROLINE AND Δ1 PIPERIDEINE: 1,3 DIPOLAR AND ANIONIC REACTIVITIES.
Mkairi, Ahmed,Hamelin, Jack
, p. 1397 - 1400 (2007/10/02)
The α-activated Δ1 pyrroline 4 and Δ1 piperideine 5 are synthesized.By thermal reaction with alkenes they give 1,3 dipolar cycloadducts and their anions lead to alkylation products.
