28525-69-1Relevant articles and documents
Organocatalytic, Organic Oxidant Promoted, Enamine C?H Oxidation/Cyclopropanation Reaction
Bond?i?, Aleksandra M.,Bond?i?, Bojan P.,D?ambaski, Zdravko,Kokotos, Christoforos G.,Triandafillidi, Ierasia
supporting information, p. 4002 - 4008 (2021/07/06)
Herein, we demonstrate that organic, single-electron oxidant in the presence of diarylprolinol silylether type catalyst serves as a tool for the transformation of electron-rich enamines to iminium ions. These iminium ions take part in a subsequent Michael-initiated ring-closure (MIRC) reaction with in situ present nucleophile giving rise to overall cyclopropanation reaction of saturated aldehydes. Stereodefined cyclopropanes are obtained in high yields and selectivities. This one-pot transformation represents the additional example of saturated aldehydes being used in the coupled one-pot processes. (Figure presented.).
Synthesis of Antitricyclic Morpholine Derivatives through Iodine(III)-Mediated Intramolecular Umpolung Cycloaddition of Olefins
Deng, Qingfu,Feng, Yangyang,Xiong, Ruimei,Xiong, Yan,Yang, Chenglin,Zhang, Xiaohui
, p. 4500 - 4506 (2020/04/09)
A (diacetoxyiodo)benzene-mediated intramolecular cycloaddition of olefins to construct tricyclic morpholines is presented. A series of substituted tricyclic morpholines were obtained in one-step simple operation under mild conditions, and the NMR studies
Enantioselective Organocatalytic Enamine C?H Oxidation/Diels- Alder Reaction
D?ambaski, Zdravko,Tzaras, Dimitrios-Ioannis,Lee, Sunggi,Kokotos, Christoforos G.,Bondzic, Bojan P.
supporting information, p. 1792 - 1797 (2019/02/25)
α,β-unsaturated aldehydes have been traditionally used in LUMO lowering asymmetric aminocatalysis (iminium catalysis), while the use of saturated aldehydes as substrates in this type of catalysis has been elusive, until recently. Herein, we demonstrate that organic, single-electron oxidants in the presence of diarylprolinol silylether type catalysts serve as effective tools for the transformation of electron rich enamines to iminium ions which partake in a subsequent Diels-Alder reaction. This enantioselective one-pot transformation represents the first example of saturated aldehydes being used in domino Diels-Alder reaction processes and demonstrates the power of this protocol for construction of stereo-defined chiral compounds and building blocks. (Figure presented.).