79164-23-1Relevant academic research and scientific papers
Nickel-Catalyzed Carboxylation of Conjugated Dienes with Carbon Dioxide and DIBAL-H for the Synthesis of β,γ-Unsaturated Carboxylic Acids
Luo, Ying,Chan, Bun,Fukuda, Tsutomu,Onodera, Gen,Kimura, Masanari
, p. 1551 - 1554 (2021)
Conjugated dienes underwent Ni-catalyst-promoted 1,2-hydrocarboxylation in a 1:1 ratio with carbon dioxide under atmospheric pressure in the presence of diisobutylaluminum hydride (DIBAL-H) to give the corresponding β,γ-unsaturated carboxylic acids, without dimerization or oligomerization of the conjugated diene.
The synthesis of an aziridinyl analogue of unit A of cryptophycin-1
Mezrai,Drici,Lesur,Kajima Mulengi,Wadouachi,Pilard
, p. 259 - 267 (2014/05/20)
A novel analogue of unit A of cryptophycin-1 was prepared starting from commercial trans-cinnamaldehyde. The modifications introduced into the new structure related to the replacement of the epoxide with an aziridine moiety, and the inclusion of the 1,3-enone moiety into an aromatic ester frame through the synthesis of a key aromatic ketone. Asymmetry was induced during the later steps of the synthetic pathway. The optical purity of compounds was monitored by chiral HPLC and polarimetric measurements.
New preparation of (Z)-1-phenyl-3-cyano-2-propen-1-ones
Trabulsi, Houssam,Rousseau, Gerard
experimental part, p. 2123 - 2134 (2011/07/09)
Reaction of γ-phenyl-β,γ-unsaturated hydroxamates with bis(collidine)-bromine(I) hexafluorophosphate led to the formation of cyclic bromo imidates. Reaction of these with triethylamine led to the formation of 3-cyano-2-propen-1-ones with good yields by a
Electrochemical carboxylation of benzylic carbonates: Alternative method for efficient synthesis of arylacetic acids
Ohkoshi, Masashi,Michinishi, Jun-Ya,Hara, Shoji,Senboku, Hisanori
experimental part, p. 7732 - 7737 (2010/10/21)
Electrochemical carboxylation of benzylic carbonates was successfully performed as an alternative method for the synthesis of phenylacetic acids by using a one-compartment cell equipped with a Pt plate cathode and an Mg rod anode in CH3CN to afford the corresponding phenylacetic acids in good yields.
2-(Trimethylsilyl)-1,3-dithiane 1-oxide as a convenient reagent for the transformation of aldehydes and ketones into homologous carboxylic acids
Krohn, Karsten,Cludius-Brandt, Stephan
experimental part, p. 2616 - 2620 (2010/09/10)
Aldehydes and ketones were converted into the corresponding homologous carboxylic acids in two steps by treatment with 2-(trimethylsilyl)-1,3-dithiane 1-oxide. A modified Peterson olefination of the carbonyl compounds gave ketene thioacetal sulfoxides that were readily cleaved in acidic acetonitrile to give the required carboxylic acids. Georg Thieme Verlag Stuttgart New York.
Facile synthesis of(e)-4-aryl-2-methyl-3-butenoic acids and their methyl esters by the condensation of tiglic acid dianion with arynes
Tran, Long,Rakeb Deshmukh,Biehl, Ed
, p. 963 - 971 (2007/10/03)
The condensation of various arynes with tiglic acid dianion yields (E)-4-aryl-2-methyl-3-butenoic acids exclusively, after proton quench. These acids were characterized as their methyl esters, which were prepared by treating the acids with diazomethane.
Temperature-Dependent Alkylation of γ-Phenyl β,γ-Unsaturated Acid and Ester Systems in Hexamethylphosphortriamide-Tetrahydrofuran Solutions Using Lithium Diisopropylamide
Veen, Reinout H. van der,Cerfontain, Hans
, p. 342 - 346 (2007/10/02)
The reactivities of some β,γ-unsaturated carboxylic acids and their methyl esters toward alkylation with methyl iodide using the lithium diisopropylamide-hexamethylphosphortriamide (LDA-HMPT) systems in THF have been investigated.The methylation selectivity of pent-3-enoic acid (2) and (1,2-dihydro-3-naphtyl)acetic acid (6) on using 1.0 equiv. of methyl iodide is high, the α-mono- to α,α-dimethylation ratios at -78 deg C being >20.The selectivity is substantially lower for styrylacetic acid (4) and increases with increasing temperature from 2.3 at -78 deg C to 8.5 at -10 deg C.The occurrence of dimethylation is ascribed to intermolecular proton exchange between the monomethylated species IIa and the nonmethylated species Ia.For the β,γ-unsaturated esters the methylation selectivity is somewhat higher than that for the corresponding carboxylic acids.
