185760-59-2Relevant academic research and scientific papers
Carbonylative Transformation of Allylarenes with CO Surrogates: Tunable Synthesis of 4-Arylbutanoic Acids, 2-Arylbutanoic Acids, and 4-Arylbutanals
Wu, Fu-Peng,Li, Da,Peng, Jin-Bao,Wu, Xiao-Feng
, p. 5699 - 5703 (2019/08/01)
In this Communication, procedures for the selective synthesis of 4-arylbutanoic acids, 2-arylbutanoic acids, and 4-arylbutanals from the same allylbenzenes have been developed. With formic acid or TFBen as the CO surrogate, reactions proceed selectively and effectively under carbon monoxide gas-free conditions.
Direct Synthesis of Polysubstituted Aldehydes via Visible-Light Catalysis
Wu, Fengjin,Wang, Leifeng,Chen, Jiean,Nicewicz, David A.,Huang, Yong
supporting information, p. 2174 - 2178 (2018/02/06)
Aldehydes are among the most versatile functional groups for synthetic chemistry. However, access to polysubstituted alkyl aldehydes is very limited and requires lengthy synthetic routes that involve multiple-step functional-group conversion. This paper reports a one-step synthesis of polysubstituted aldehydes from readily available olefin substrates using visible-light photoredox catalysis. Despite a number of competing reaction pathways, commercial styrenes react with vinyl ethers selectively in the presence of an acridinium salt photooxidant and a disulfide hydrogen-atom-transfer catalyst under blue LED irradiation. Alkyl aldehydes with different substitution patterns are prepared in good yields. This strategy can be applied to structurally sophisticated substrates.
Tunable P-Chiral Bisdihydrobenzooxaphosphole Ligands for Enantioselective Hydroformylation
Tan, Renchang,Zheng, Xin,Qu, Bo,Sader, C. Avery,Fandrick, Keith R.,Senanayake, Chris H.,Zhang, Xumu
supporting information, p. 3346 - 3349 (2016/07/26)
Air-stable and tunable chiral bisdihydrobenzooxaphosphole ligands (BIBOPs) were employed in rhodium-catalyzed asymmetric hydroformylation of various terminal olefins with excellent conversions (>99%), moderate-to-excellent enantioselectivities (up to 95:5 er), and branched to linear ratios (b:l) of up to 400.
Terminal olefins to chromans, isochromans, and pyrans via allylic C-H oxidation
Ammann, Stephen E.,Rice, Grant T.,White, M. Christina
supporting information, p. 10834 - 10837 (2014/08/18)
The synthesis of chroman, isochroman, and pyran motifs has been accomplished via a combination of Pd(II)/bis-sulfoxide C-H activation and Lewis acid co-catalysis. A wide range of alcohols are found to be competent nucleophiles for the transformation under uniform conditions (catalyst, solvent, temperature). Mechanistic studies suggest that the reaction proceeds via initial C-H activation followed by a novel inner-sphere functionalization pathway. Consistent with this, the reaction shows reactivity trends orthogonal to those of traditional Pd(0)-catalyzed allylic substitutions.
Preparation of cis-5-methoxy-and-7-methoxy-1-acetoxy-1,2,3,4,4a,10a- hexahydro-9(10H)-phenanthrenone. An epoxide-arene reaction involving a selective 1,2-alkyl shift rearrangement
Garg, Neeraj,Gogoll, Adolf,Westerlund, Christer,Sundell, Staffan,Karlen, Anders,Hallberg, Anders
, p. 15209 - 15224 (2007/10/03)
The preparation of cis-1α-acetoxy-7-methoxy-1,2,3,4,4a,10a-hexahydro-9(10H)-phenanthrenone 5 was accomplished starting from 6-methoxy-1-tetralone. Reduction of 7-methoxy-1,2,3, 4,9,10-hexahydro-1-oxo-phenanthrene 8, acetylation and subsequent oxidation delivered 5, Application of an analogus procedure to the preparation of cis-1β-acetoxy-5-methoxy-1,2,3,4,4a,10a-hexahydro-9(10H)-phenanthrenone 6 was not feasible. A more elaborate route was developed for the synthesis of compound 6, where an epoxide-arene reaction involving a 1,2-alkyl shift rearrangement, constituted a highly selective key transformation.
OXYGEN HETEROCYCLES BY SULPHUR YLIDE ANNULATION. X. 3-HYDROXY-3,4,5,6-TETRAHYDRO-2H-1-BENZOXOCINS FROM 2-(4-OXOALKYL)PHENOLS AND DIMETHYLSULPHOXONIUM METHYLIDE
Arnone, Alberto,Bernardi, Rosanna,Bravo, Pierfrancesco,Frigerio, Massimo,Ticozzi, Calimero
, p. 87 - 94 (2007/10/02)
The synthesis of several 3-hydroxy-3,4,5,6-tetrahydro-2H-1-benzoxocins, 7, by dimethylsulphoxonium methylide reaction on 2-(4-oxoalkyl)phenols, 5, obtained in turn from o-benzyloxybenzaldehydes, 1, is reported.The formation of intermediate open-chain oxiranes 6 arising by a transfer of methylene from the ylide to the carbonyl group of the substrate and the highly regiospecific endo intramolecular cyclization to 3-hydroxy-3,4,5,6-tetrahydro-2H-1-benzoxocins, 7, have been followed by 1H NMR spectroscopy.The synthesis of the isomeric 2-hydroxymethyl-2,3,4,5-tetrahydro-1-benzoxepins, 9, from the same 2-(4-oxoalkyl)phenols, through methylenation by triphenylphosphonium methylide and MCPBA oxidation is also reported.Dehydration of the title compounds afforded dihydrobenzoxocins 11 - 13 which, upon catalytic hydrogenation, gave 3,4,5,6-tetrahydro-1-benzoxocins 14.A detailed 1H NMR study allowed assignment of the configurations and the preferred conformations of some tetrahydrobenzoxocins and tetrahydrobenzoxepins trisubstituted on the heterocyclic ring.
