115476-97-6Relevant academic research and scientific papers
Effect of Microwave Irradiation on the Direction and Stereochemistry of Rodionov and Michael Reactions
Romanova,Gravis,Kudan,Leshcheva,Zyk
, p. 692 - 697 (2003)
The reactions of 2-phenylpropanal with ethyl hydrogen malonate and benzylamine (or benzyl-ammonium acetate) and of ethyl 4-phenyl-2-pentenoate with benzylamine take different pathways, depending on the conditions.
An easy, efficient, and completely stereoselective synthesis of (E)-α,β-unsaturated esters via sequential aldol-type/elimination reactions promoted by samarium diiodide or chromium dichloride
Concellon, Jose M.,Concellon, Carmen,Mejica, Carmen
, p. 6111 - 6113 (2005)
(E)-α,β-Unsaturated esters can be obtained with complete stereoselectivity by reaction of different aldehydes and ethyl clibromoacetate promoted by SmI2 or CrCl2. The transformation takes place as two sequential reactions: an aldol-type reaction and a β-elimination reaction.
Palladium-catalyzed double-bond migration of unsaturated hydrocarbons accelerated by tantalum chloride
Murai, Masahito,Nishimura, Kengo,Takai, Kazuhiko
supporting information, p. 2769 - 2772 (2019/03/23)
The operationally simple palladium-catalyzed double-bond migration without heteroatom-containing coordinating functional groups is described. Addition of TaCl5 as a second catalyst greatly enhanced the migration efficiency to provide β-alkylsty
Organo-Catalyzed Regio- and Geometry-Specific Construction of β-Hydroxyl-α-vinyl Carboxylic Esters: Substrate Scope, Mechanistic Insights, and Applications
Chai, Yonghai,Zhou, Jinjin,Wu, Yanbin,Feng, Yingle,Wang, Panru,Chen, Yange,Wang, Xinying,Zhao, Beibei,Zhang, Qi
, p. 10476 - 10486 (2018/09/06)
A green protocol has been developed for the synthesis of β-hydroxyl-α-vinyl carboxylic esters using aldehydes and α,β-unsaturated esters bearing an activated γ proton as starting materials under Morita-Baylis-Hillman (MBH) reaction conditions. Diverse β-hydroxyl-α-vinyl carboxylic esters have been synthesized regiospecifically in moderate to good yields with only E geometric selectivity. Other remarkable features include atom efficiency, environmental benignancy, and mild reaction conditions. Furthermore, the reaction products could be readily converted into tetrahydrofuran, dihydrofuran, and furan derivatives.
Facile synthesis of α, β-unsaturated esters through a one-pot copper-catalyzed aerobic oxidation-Wittig reaction
Ren, Cheng,Shi, Zhenyu,Ding, Weijie,Liu, Zhiqing,Jin, Huile,Yu, Xiaochun,Wang, Shun
supporting information, p. 14 - 17 (2017/12/06)
An efficient one-pot synthesis of α, β-unsaturated esters through the aerobic oxidation – Wittig tandem reaction of alcohols and phosphorous ylide is developed. This new method operates under mild reaction conditions, and uses CuI/TEMPO (TEMPO = 2,2,6,6-tetramethylpiperidine-N-oxyl) as co-catalyst and air (O2) as the oxidant. It tolerates a wide range of functionalized benzylic alcohol and aliphatic alcohols.
Regio- and Stereocontrol in the Reactions of α-Halo-β,γ-enoates and α- O -Phosphono-β,γ-enenitriles with Organocuprates
Dieter, R. Karl,Picado, Alfredo
, p. 11125 - 11138 (2015/02/19)
The reactions of (Z)- and (E)-ethyl 2-chloro-3-octenoate (4a and 17) and (E)- and (Z)-diethyl (1-cyano-2-heptenyl)phosphate (21a and 21b) with organocuprates were investigated as potential substrates for preparing γ-substituted α,β-enoates and enenitriles. In these copper-mediated allylic substitution reactions, the Z-isomer 4a displayed complete regio- and stereoselectivity (i.e., E:Z), while the regio- and stereoselectivity for E-isomer 17 varied as a function of solvent, cuprate reagent, transferable ligand, and cuprate counterion (e.g., Li+ vs MgX+). Excellent selectivities could be achieved with 17 and nBuCuCNLi in Et2O. Conditions for improved selectivities in the reactions of allylic cyanophosphates over those previously reported were found. A series of relative rate and competition experiments was performed, and the degree of regio- and stereoselectivity for each system was rationalized in the light of the current mechanistic understanding of cuprate-mediated allylic substitution reactions.
Copper-catalyzed decarboxylative trifluoromethylation of allylic bromodifluoroacetates
Ambler, Brett R.,Altman, Ryan A.
supporting information, p. 5578 - 5581 (2013/11/19)
The development of new synthetic fluorination reactions has important implications in medicinal, agricultural, and materials chemistries. Given the prevalence and accessibility of alcohols, methods to convert alcohols to trifluoromethanes are desirable. However, this transformation typically requires four-step processes, specialty chemicals, and/or stoichiometric metals to access the trifluoromethyl-containing product. A two-step copper-catalyzed decarboxylative protocol for converting allylic alcohols to trifluoromethanes is reported. Preliminary mechanistic studies distinguish this reaction from previously reported Cu-mediated reactions.
A newly-designed PE-supported arsine for efficient and practical catalytic Wittig olefination
Wang, Peng,Liu, Chun-Rong,Sun, Xiu-Li,Chen, Shuai-Shuai,Li, Jun-Fang,Xie, Zuowei,Tang, Yong
supporting information; experimental part, p. 290 - 292 (2012/01/06)
A newly designed PE-supported arsine has been developed as an excellent catalyst for catalytic Wittig-type olefination. Simple ketones, in particular inactive ketones prove to be suitable substrates for the first time. This reaction provides an easy access to di-, tri-, and tetra-substituted olefins in high yield.
Highly selective reactions of unbiased alkenyl halides and alkylzinc halides: Negishi-plus couplings
Krasovskiy, Arkady,Lipshutz, Bruce H.
scheme or table, p. 3822 - 3825 (2011/09/20)
High yielding stereo- and chemoselective Pd-catalyzed cross-couplings in THF at room temperature of alkenyl iodides and bromides with primary and secondary alkyl zinc iodides have been developed with the aid of N-methyimidazole as the key additive.
Highly (E)-selective wadsworth-emmons reactions promoted by methylmagnesium bromide
Claridge, Timothy D. W.,Davies, Stephen G.,Lee, James A.,Nicholson, Rebecca L.,Roberts, Paul M.,Russell, Angela J.,Smith, Andrew D.,Toms, Steven M.
body text, p. 5437 - 5440 (2009/06/18)
(Chemical Equation Presented) An experimentally simple protocol for the very highly (E)-selective Wadsworth-Emmons reaction [(E):(Z) selectivities in excess of 180:1 in some cases] of a range of straight-chain and branched aliphatic, substituted aromatic, and base-sensitive aldehydes via reaction with an alkyl diethylphosphonoacetate and MeMgBr is reported.
