1617-31-8Relevant academic research and scientific papers
Metabolic coupling of dehydration and decarboxylation in the curacin A pathway: Functional identification of a mechanistically diverse enzyme pair
Gu, Liangcai,Jia, Junyong,Liu, Haichuan,Hakansson, Kristina,Gerwick, William H.,Sherman, David H.
, p. 9014 - 9015 (2006)
This study describes the functional identification of a pair of mechanistically diverse enzymes that catalyze the successive dehydration (CurE ECH1) and decarboxylation (CurF ECH2) of (S)-HMG-ACP to generate a 3-methylcrotonyl-ACP intermediate, the presumed precursor of the cyclopropyl ring in curacin A. The reactions catalyzed by ECH1 and ECH2 are found in a broad cross-section of microbial natural product gene clusters and participate in the introduction of carbon chain branch points and functional group diversity as key steps in the HMG-CoA synthase mediated addition of C-2 from acetate to the β-carbonyl group of polyketide chains. Copyright
EFFICIENT PREPARATION OF ALLYLIC GRIGNARD REAGENTS USING SLURRIES OF PRECONDENSED MAGNESIUM
Oppolzer, Wolfgang,Kuendig, Ernest Peter,Bishop, Paul M.,Perret, Celia
, p. 3901 - 3904 (1982)
Using a simple apparatus addition of 2-alkenyl halides to precondensed active Mg in THF gave clean solutions of 2-alkenylmagnesium halides which on carbonation furnished β,γ-unsaturated carboxylic acid in high yields.
Reaction of Diketene with Grignard Reagents in the Presence of Cobalt Catalyst. A Convenient Method for the Synthesis of 3-Methylenealkanoic Acids Leading to Terpenoids
Fujisawa, Tamotsu,Sato, Toshio,Gotoh, Yoshihiko,Kawashima, Masatoshi,Kawara, Tatsuo
, p. 3555 - 3559 (1982)
Primary alkyl Grignard reagents react regioselectively with diketene in the presence of cobalt(II) iodide to afford 3-methylenealkanoic acids in good yields.The synthetic utility of this reaction is demonstrated in the syntheses of terpenoids by two methods.Utilizing the isomerization of double bond of 3-methylenealkanoic acids, geranic acid and farnesic acid were obtained in two steps.Another method, the tandem sigmatropic rearrangement of the corresponding allylic esters was used for the synthesis of C18-Cecropia juvenile hormone.
Palladium-Catalyzed, Atmospheric Pressure Carbonylation of Allylic Chlorides in Two-Phase Aqueous Sodium Hydroxide-Organic Solvent Media
Kiji, Jitsuo,Okano, Tamon,Nishiumi, Wataru,Konishi, Hisatoshi
, p. 957 - 960 (1988)
The palladium-catalyzed, atmospheric pressure carbonylation of allylic chlorides is realized in aqueous NaOH/benzene.Phosphine complexes PdCl2L2 (I) (a, L=Ph2P(m-C6H4SO3Na; b, L=Ph3P), or Na2PdCl4 can be used as the catalyst.
Ether cleavage by activated metals II.* Cleavage of allyl and benzyl ethers by activated magnesium
Bartmann, Ekkehard
, p. 19 - 24 (1987)
Activated magnesium (prepared by reduction of magnesium halides with potassium) reacts with allyl and benzyl ethers to give the corresponding allyl or benzyl magnesium compounds.
Silver encapsulated copper salen complex: Efficient catalyst for electrocarboxylation of cinnamyl chloride with CO2
Wu, La-Xia,Zhao, Ying-Guo,Guan, Ye-Bin,Wang, Hui,Lan, Yang-Chun,Wang, Huan,Lu, Jia-Xing
, p. 32628 - 32633 (2019)
An active catalyst, [Cu]?Ag composite, was synthesized for the first time and used as a cathode for electrocarboxylation of cinnamyl chloride with CO2. β,γ-Unsaturated carboxylic acids were obtained with excellent yield and moderate selectivity. Moreover, reasonable yields and selectivities of carboxylic acids were also achieved with several allylic halides and aryl halides.
Organophotoredox/Copper Hybrid Catalysis for Regioselective Allylic Aminodecarboxylation of β,γ-Unsaturated Carboxylic Acids
Manick, Anne-Doriane,Tanaka, Hirotaka,Oisaki, Kounosuke,Kanai, Motomu
, p. 2936 - 2947 (2018)
A new cooperative organophotoredox/copper catalysis allowing for the conversion of β,γ-unsaturated carboxylic acids into allylic hydrazides via radical regioselective allylic decarboxylative amination is reported. The coexistence of the copper catalyst is essential for the high yield and regioselectivity.
Synthesis of the sex pheromone of the citrus mealybug, Pseudococcus cryptus
Nakahata, Takashi,Itagaki, Noriaki,Arai, Tomonori,Sugie, Hajime,Kuwahara, Shigefumi
, p. 2627 - 2631 (2003)
The sex pheromone of the citrus mealybug (Pseudococcus cryptus), [(1R,3R)-3-isopropenyl-2,2-dimethylcyclobutyl]methyl 3-methyl-3-butenoate, was synthesized from (+)-α-pinene in five operational steps in a 43% overall yield. The synthetic pheromone was identical with the natural pheromone in 1H-NMR and mass spectroscopic properties, and showed almost the same pheromonal activity as the natural pheromone.
Catalytic, contra-Thermodynamic Positional Alkene Isomerization
Occhialini, Gino,Palani, Vignesh,Wendlandt, Alison E.
supporting information, p. 145 - 152 (2022/01/19)
The positional isomerization of C═C double bonds is a powerful strategy for the interconversion of alkene regioisomers. However, existing methods provide access to thermodynamically more stable isomers from less stable starting materials. Here, we report
Nickel-catalyzed electrocarboxylation of allylic halides with CO2
Wu, La-Xia,Deng, Fang-Jie,Wu, Lin,Wang, Huan,Chen, Tai-Jie,Guan, Ye-Bin,Lu, Jia-Xing
, p. 13137 - 13141 (2021/08/03)
Nickel-catalyzed regioselective electrocarboxylation of allylic halides with CO2at atmospheric pressure has been developed by adjusting reaction parameters, including catalyst, solvent, temperature and additive. β,γ-Unsaturated carboxylic acids were obtained in moderate to good yields and with high chain selectivity. This reaction shows tolerance to functional groups. In addition, cyclic voltammetry was performed to provide the possible mechanism of nickel-catalyzed CO2allylation.
