141-27-5Relevant articles and documents
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Ishitsuka,M. et al.
, p. 1269 - 1272 (1979)
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Total Synthesis of (-)-Phorbaketal A
Joung, Seewon,Kim, Rira,Lee, Hee-Yoon
, p. 3903 - 3906 (2017)
A convergent asymmetric total synthesis of phorbaketal A was achieved in 10 steps through a Au(I)-catalyzed intramolecular spiroketalization reaction of an alkyne diol intermediate prepared from (R)-carvone and geranial. The spiroketalization reaction was
Structure of sargatriol, a new isoprenoid chromenol from a marine alga: Sargassum tortile
Kikuchi,Mori,Yokoi,et al.
, p. 690 - 692 (1975)
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Asymmetric total synthesis of ieodomycin B
Lin, Shuangjie,Zhang, Jianting,Zhang, Zhibin,Xu, Tianxiang,Huang, Shuangping,Wang, Xiaoji
, (2017)
Ieodomycin B, which shows in vitro antimicrobial activity, was isolated from a marine Bacillus species. A novel asymmetric total synthetic approach to ieodomycin B using commercially available geraniol was achieved. The approach involves the generation of 1,3-trans-dihydroxyl at C-3 and C-5 positions via a Crimmins-modified Evans aldol reaction and a chelation-controlled Mukaiyama aldol reaction of a p-methoxybenzyl-protected aldehyde, as well as the generation of a lactone ring in a deprotection-lactonization one-pot reaction.
Highly efficient aerobic oxidation of benzylic and allylic alcohols by a simple catalyst system of [RuCl2(p-cymene)]2/Cs2CO3
Lee,Chang
, p. 7507 - 7510 (2000)
A new catalyst system of [RuCl2(p-cymene)]2/Cs2CO3 has been disclosed for highly efficient aerobic oxidation of activated alcohols to the corresponding carbonyl compounds, which is characterized by its high selectivity and activity, operational simplicity, and low air and moisture sensitivity. (C) 2000 Elsevier Science Ltd.
Pt-Catalyzed selective oxidation of alcohols to aldehydes with hydrogen peroxide using continuous flow reactors
Kon, Yoshihiro,Nakashima, Takuya,Yada, Akira,Fujitani, Tadahiro,Onozawa, Shun-Ya,Kobayashi, Shū,Sato, Kazuhiko
supporting information, p. 1115 - 1121 (2021/02/16)
The oxidation of alcohols to aldehydes is a powerful reaction pathway for obtaining valuable fine chemicals used in pharmaceuticals and biologically active compounds. Although many oxidants can oxidize alcohols, only a few hydrogen peroxide oxidations can be employed to continuously synthesize aldehydes in high yields using a liquid-liquid two-phase flow reactor, despite the possibility of the application toward a safe and rapid multi-step synthesis. We herein report the continuous flow synthesis of (E)-cinnamaldehyde from (E)-cinnamyl alcohol in 95%-98% yields with 99% selectivity for over 5 days by the selective oxidation of hydrogen peroxide using a catalyst column in which Pt is dispersed in SiO2. The active species for the developed selective oxidation is found to be zero-valent Pt(0) from the X-ray photoelectron spectroscopy measurements of the Pt surface before and after the oxidation. Using Pt black diluted with SiO2as a catalyst to retain the Pt(0) species with the optimal substrate and H2O2introduction rate not only enhances the catalytic activity but also maintains the activity during the flow reaction. Optimizing the contact time of the substrate with Pt and H2O2using a flow reactor is important to proceed with the selective oxidation to prevent the catalytic H2O2decomposition.
Selective aerobic oxidation of benzylic and allylic alcohols catalyzed by Cu(OAc)2/TEMPO/Et2NH
Pasupuleti, Bala Gangadhar,Gogoi, Achinta,Bez, Ghanashyam
, p. 589 - 597 (2021/09/28)
Selective oxidation of benzylic and allylic alcohols to their corresponding aldehyde/ketone derivative without affecting saturated alcohols is still a challenging endeavor in organic synthesis. Various metal complexes, especially the copper complexes in the presence of TEMPO are being used very often for such transformations under aerobic conditions, but they are not selective to allylic and benzylic alcohols. The use of copper salt for oxidation of alcohols in the absence of a ligand are very scarcely studied except for the one catalyzed by CuCl/TEMPO where chloride inhibition and lack of selective oxidation have been noted upon use of CuCl2. Herein we report a Cu(OAc)2 catalyzed and TEMPO mediated selective aerobic oxidation of benzylic and allylic alcohols to aldehyde/ketone in the presence of Et2NH. The method avoids pre-synthesis of the catalyst as in the case of Cu(II)/(I) complexes/TEMPO catalyzed oxidation reactions, requires low catalyst loading, employs cheaper copper salt, and gives excellent selectivity for oxidation of benzylic and allylic alcohols.