- Metal-Free 2,2,6,6-tetramethylpiperidin-1-yloxy radical (TEMPO) catalyzed aerobic oxidation of hydroxylamines and alkoxyamines to oximes and oxime ethers
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TEMPO-Mediated oxidation of hydroxylamines (=hydroxyamines) and alkoxyamines to the corresponding oxime derivatives is reported (TEMPO=2,2,6,6-tetramethylpiperidin-1-yloxy radical; Scheme 2). These environmentally benign oxidations proceed in good to excellent yields (Table 1). For alkoxyamines, oxidation to the corresponding oxime ethers can be performed by using dioxygen as a terminal oxidant in the presence of 5-10 mol-% of TEMPO or 4-substituted derivatives thereof as a catalyst (Scheme 3 and Table 2). Importantly, benzyl bromides can directly be transformed to oxime ethers via in situ alkoxyamine formation by a nucleophilic substitution followed by TEMPO-mediated oxidation (Scheme 4 and Table 3). Copyright
- Wertz, Sebastian,Studer, Armido
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p. 1758 - 1772,15
(2012/12/13)
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- Total synthesis of (-)-martinellic acid via radical addition-cyclization- elimination reaction
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(Chemical Equation Presented) The asymmetric total synthesis of martinellic acid, the first pyrrolo[3,2-c]quinoline alkaloid found in nature, is described. Three key steps in our synthesis of (-)-martinellic acid are the Bu 3SnH-promoted radica
- Shirai, Atsushi,Miyata, Okiko,Tohnai, Norimitsu,Miyata, Mikiji,Procter, David J.,Sucunza, David,Naito, Takeaki
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p. 4464 - 4475
(2008/09/21)
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- An improved synthesis of (-)-martinellic acid via radical addition-cyclization-elimination reaction of chiral oxime ether
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A concise formal synthesis of (-)-martinellic acid has been accomplished by preparing optically active dipyrroloquinoline as a key synthetic intermediate, which was prepared via the radical addition-cyclization-elimination of oxime ether carrying an unsaturated ester followed by two chemoselective reductions of the carbonyl groups. Georg Thieme Verlag Stuttgart.
- Miyata, Okiko,Shirai, Atsushi,Yoshino, Shintaro,Takeda, Yoshifumi,Sugiura, Makiko,Naito, Takeaki
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p. 893 - 896
(2007/10/03)
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