135286-01-0Relevant articles and documents
In Situ Conformational Fixation of the Amide Bond Enables General Access to Medium-Sized Lactams via Ring-Closing Metathesis
Hegmann, Nina,Prusko, Lea,Diesendorf, Nina,Heinrich, Markus R.
, p. 7825 - 7829 (2018)
In this work, a novel phenethylamine-derived protecting group is introduced, which is able to significantly enhance the Grubbs I-catalyzed formation of 9- to 12-membered lactams through charge-induced conformational fixation under acidic conditions. As the new approach is particularly valuable for 10- and 11-membered ring systems, for which no related precedence was available so far, the overall strategy now offers general access to medium-sized lactams via ring closing metathesis. Cleavage of the protecting group can be achieved through a mild sequence combining N-oxidation and Cope elimination or alternatively under standard hydrogenation conditions.
Regiospecific Conversion of Oxiranes into Primary Alcohols via Reaction with Organotin Derivatives
Fiorenza, Mariella,Ricci, Alfredo,Taddei, Maurizio,Tassi, Daniele,Seconi, Giancarlo
, p. 640 - 641 (1983)
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C-H Functionalization of Amino Alcohols by Osmium Tetroxide/NMO or TPAP/NMO: Protecting Group-Free Synthesis of Indolizidines (–)-223AB and 3-epi-(–)-223AB
Chen, Wei-Lun,Wang, Lee-Ya,Li, Yu-Jang
supporting information, p. 103 - 107 (2020/01/02)
The oxidative cyclization of amino alcohols by osmium tetroxide/NMO or tetrapropylammonium perruthenate (TPAP)/NMO was found to provide an N,O-acetal moiety through the trapping of the resulting iminium ion by the alcohol. These two transformations were demonstrated in the synthesis of indolizidines (–)-223AB and 3-epi-(–)-223AB.
Manganese Complexes of Pyrrole- and Indolecarboxamide Ligands: Synthesis, Structure, Electrochemistry, and Applications in Oxidative and Lewis-Acid-Assisted Catalysis
Yadav, Sunil,Kumar, Sushil,Gupta, Rajeev
, p. 5534 - 5544 (2015/12/01)
This work shows the synthesis and structural, spectroscopic, and electrochemical properties of MnIII complexes supported with pyrrole- and indolecarboxamide ligands. In all cases, the respective ligand constitutes a N4 coordination sphere about the MnIII ion. The MnIII complexes of pyrrolecarboxamide ligands are square pyramidal with a fifth Cl atom, whereas analogous complexes of indolecarboxamide ligands are essentially square planar. Electrochemical studies reveal highly negative MnIII/II and moderately positive MnIV/III redox potentials. In situ generated Mn4+ species of the pyrrolecarboxamide ligands were characterized by absorption and electron paramagnetic resonance spectroscopy. All complexes functioned as catalysts in olefin epoxidation reactions by using PhIO as the oxo-transfer agent. All complexes also acted as Lewis acid catalysts for ring-opening reactions of assorted epoxides with various nucleophiles. We also show a one-pot, two-step epoxidation reaction followed by ring opening, which illustrates the catalytic significance of the present complexes. Importantly, MnIII complexes carrying electron-donating substituents on the ligand were found to be better catalysts.