26908-23-6Relevant articles and documents
A concise asymmetric total synthesis of (+)-brevisamide
Herrmann, Aaron T.,Martinez, Steven R.,Zakarian, Armen
, p. 3636 - 3639 (2011)
A new protecting-group-free synthesis of the marine monocyclic ether (+)-brevisamide is reported. The enantioselective synthesis utilizes a key asymmetric Henry reaction and an Achmatowicz rearrangement for the formation of the tetrahydropyran ring. A pen
The furan approach to azacyclic compounds
García, Isela,Pérez, Manuel,Gándara, Zoila,Gómez, Generosa,Fall, Yagamare
, p. 3609 - 3612 (2008)
We describe an efficient new approach to the synthesis of azacyclic compounds that extends our recently developed methodology based on the oxidation of a furan ring with singlet oxygen followed by an intramolecular hetero Michael addition. The new approac
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Peshekhonova,Ponomarev
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Ponomarev et al.
, (1966)
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Hofmann et al.
, p. 191,194 (1947)
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Manganese=Catalyzed Achmatowicz Rearrangement Using Green Oxidant H2O2
Xing, Qingzhao,Hao, Zhe,Hou, Jing,Li, Gaoqiang,Gao, Ziwei,Gou, Jing,Li, Chaoqun,Yu, Binxun
, p. 9563 - 9586 (2021/07/20)
Oxidation reactions have been extensively studied in the context of the transformations of biomass=derived furans. However, in contrast to the vast literature on utilizing the stoichiometric oxidants, such as m=CPBA and NBS, catalytic methods for the oxidative furan=recyclizations remain scarcely investigated. Given this, we report a means of manganese=catalyzed oxidations of furan with low loading, achieving the Achmatowicz rearrangement in the presence of hydrogen peroxide as an environmentally benign oxidant under mild conditions with wide functional group compatibility.
Highly pH-Dependent Chemoselective Transfer Hydrogenation of α,β-Unsaturated Aldehydes in Water
Luo, Nianhua,Liao, Jianhua,Ouyang, Lu,Wen, Huiling,Liu, Jitian,Tang, Weiping,Luo, Renshi
, p. 3025 - 3031 (2019/08/30)
The pH-dependent selective Ir-catalyzed hydrogenation of α,β-unsaturated aldehydes was realized in water. Using HCOOH as the hydride donor at low pH, the unsaturated alcohol products were obtained exclusively, while the saturated alcohol products were formed preferentially by employing HCOONa as the hydride donor at high pH. A wide range of functional groups including electron-rich as well as electron-poor substituents on the aryl group of α,β-unsaturated aldehydes can be tolerated, affording the corresponding products in excellent yields with high TOF values. High selectivity and yields were also observed for α,β-unsaturated aldehydes with aliphatic substituents. Our mechanistic investigations indicate that the pH value is critical to the chemoselectivity.
