26928-13-2Relevant academic research and scientific papers
P[N(i-Bu)CH2CH2]3N: Nonionic Lewis base for promoting the room-temperature synthesis of α,β-unsaturated esters, fluorides, ketones, and nitriles using Wadsworth - Emmons phosphonates
Chintareddy, Venkat Reddy,Ellern, Arkady,Verkade, John G.
supporting information; experimental part, p. 7166 - 7174 (2010/12/25)
The bicyclic triaminophosphine P(RNCH2CH2) 3N (R = i-Bu, 1c) serves as an effective promoter for the room-temperature stereoselective synthesis of α,β-unsaturated esters, fluorides, and nitriles from a wide array of aromatic, aliphatic, heterocyclic, and cyclic aldehydes and ketones, using a range of Wadsworth-Emmons (WE) phosphonates. Among the analogues of 1c [R = Me (1a), i-Pr (1b), Bn (1d)], 1a and 1b performed well, although longer reaction times were involved, and 1d led to poorer yields than 1c. Functionalities such as cyano, chloro, bromo, methoxy, amino, ester, and nitro were well tolerated. We were able to isolate and characterize (by X-ray means; see above) the reactive WE intermediate species formed from 2b and 1c.
Microwave-assisted one-pot synthesis of α-fluoro-α,β- unsaturated esters under solvent-free conditions
Ren, Aishan,Yang, Xiongjun,Hong, Jing,Yu, Xiaochun
experimental part, p. 2376 - 2378 (2009/05/27)
A microwave-assisted approach for the synthesis of α-fluoro-α, β-unsaturated esters from ethyl bromofluoroacetate, aldehydes, and triphenylphosphine in the presence of Zn-Cu under solvent-free conditions was achieved. The reaction was accomplished within
An Expedient Stereoselective Access to (Z)-2-Fluoroalkenoates
Clemenceau, Denis,Cousseau, Jack
, p. 6903 - 6906 (2007/10/02)
The reaction between an aldehyde R-CHO and diethyl 2-oxo-3-fluorobutan-1,4-dioate as its sodium salt EtO2C-CO-CF-CO2Et-,Na+ mainly leads in THF to (Z)-2-fluoroalkenoates R-CH=CF-CO2Et (Z/E>/=80/20), the Z-stereoselectivity depending on the bulk of the R group.Key words: 2-Fluoroalkenoates; (Z)-stereoselective synthesis.
A convenient palladium-catalyzed synthesis of α-fluoro-α,β-unsaturated esters
Shen, Yanchang,Zhou, Yuefen
, p. 247 - 251 (2007/10/02)
During the treatment of ethyl α-fluoro-α-iodoacetate with aldehydes in the presence of tri-n-butylarsine and a catalytic amount (10 molpercent) of Pd(PPh3)4, the aldehydes were eventually completely consumed and α-fluoro-α,β-unsaturated esters were obtained in 52-90percent yield.
