49769-78-0Relevant articles and documents
Reaction of dicarbomethoxycarbene with thiophene derivatives
Jenks, William S.,Heying, Melanie J.,Stoffregen, Stacey A.,Rockafellow, Erin M.
, p. 2765 - 2770 (2009)
Photolysis of derivatives of dimethylmalonate thiophene-S,C-ylide provides dicarbomethoxycarbene, which can react with thiophene to form dimethyl (2-thienyl)malonate. By generation of dicarbomethoxycarbene from the dibenzothiophene-based ylide in neat thi
Reductive Knoevenagel Condensation with the Zn-AcOH System
Ivanov, Konstantin L.,Melnikov, Mikhail Ya.,Budynina, Ekaterina M.
, p. 1285 - 1291 (2020/11/13)
An efficient gram-scale one-pot approach to 2-substituted malonates and related structures is developed, starting from commercially available aldehydes and active methylene compounds. The technique combines Knoevenagel condensation with the reduction of the C=C bond in the resulting activated alkenes with the Zn-AcOH system. The relative ease with which the C=C bond reduction occurs can be traced to the accepting abilities of the substituents in the intermediate arylidene malonates.
Au-Cavitand Catalyzed Alkyne-Acid Cyclizations
Ho, Tam D.,Schramm, Michael P.
supporting information, p. 5678 - 5684 (2019/08/21)
Supramolecular cavitands that contain inwardly directed functional groups have yielded specialized transformations and trapping of reactive intermediates. A recently reported 3-wall Au cavitand provides exciting opportunities for supramolecular catalysis. In this study, a variety of substituted γ-alkynoic acids were reacted to give lactones. The interaction of peripheral “R” groups revealed differential catalyst behavior. Extremely large and small groups reacted with appreciable rate. Intermediate sized groups however, slowed significantly: giving support that size-specific binding is at play when using cavitands as a scaffold for gold catalysis. These results serve as some of the first evidence of the interplay between substrate and cavitand interior in the catalytic sphere.
Palladium-Catalyzed [3 + 2]-C-C/N-C Bond-Forming Annulation
Liu, Yang,Mao, Zhongyi,Pradal, Alexandre,Huang, Pei-Qiang,Oble, Julie,Poli, Giovanni
supporting information, p. 4057 - 4061 (2018/07/15)
The synthesis of bi- and tricyclic structures incorporating pyrrolidone rings is disclosed, starting from resonance-stabilized acetamides and cyclic α,β-unsaturated-γ-oxycarbonyl derivatives. This process involves an intermolecular Tsuji-Trost allylation/intramolecular nitrogen 1,4-addition sequence. Crucial for the success of this bis-nucleophile/bis-electrophile [3 + 2] annulation is its well-defined step chronology in combination with the total chemoselectivity of the former step. When the newly formed annulation product carries a properly located o-haloaryl moiety at the nitrogen substituent, a further intramolecular keto α-arylation can join the cascade, thereby forming two new cycles and three new bonds in the same synthetic operation.
