197313-84-1Relevant academic research and scientific papers
A new route to α-trifluoromethyl-α,β-unsaturated esters
Zhang, Xingang,Qing, Feng-Ling,Yang, Yonggang,Yu, Jiang,Fu, Xiang-Kai
, p. 2953 - 2955 (2000)
The treatment of α-bromo-α,β-unsaturated esters with FSO2CF2CO2Me and CuI in DMF/HMPA constitutes a new synthetic scheme for the preparation of α-trifluoromethyl-α,β-unsaturated esters. (C) 2000 Elsevier Science Ltd.
Synthesis and reactions of chiral 5-Substituted (Z)-Ethyl 2-Bromo-3-(1,3 -dioxolan-4-yl) 3-propenoates
Braun, Norbert A.,Buerkle, Ulrike,Klein, Iris,Spitzner, Dietrich
, p. 7057 - 7058 (1997)
Wittig olefination of the aldehydes 2a/b gave the 2-bromo-dienes 3a/b. Regioselective catalytic Sharpless asymmetric dihydroxylation (AD) led to the diols 4a/b with high enantiomeric excess tee > 94 %). Cascade reactions of 5a/b with dienolate 6 yielded 7
Chemoselective Bromination of Dienoates
Kobelevskaya, Valentina A.,Popov, Alexander V.,Rulev, Alexander Yu.,Zinchenko, Sergey V.
, (2020)
A variety of tetra-, di- and monobromo derivatives of dienoates were prepared from parent polyunsaturated esters under mild conditions. According to proposed protocol the target bromoesters were easily obtained as a rule in good yields and high selectivity.
One-pot combination of the wittig olefination with bromination and oxidation reactions
Karama, Usama,Mahfouz, Refat,Al-Othman, Zeid,Warad, Ismail,Almansour, Abdulrahman
, p. 893 - 898 (2013)
A simple one-pot process for in situ bromination of (ethoxycarbonylmethylene)-triphenylphosphorane 1 was carried out. This was followed by oxidation of alcohol using SO3. Pyridine complex as a mild oxidant and in situ trapping of the aldehyde. This process constitutes a stereoselective one-pot procedure for the preparation of Z-configured-bromo-,- unsaturated esters in good yield.
A facile one-pot synthesis of α-bromo-α,β-unsaturated esters from alcohols
Karama, Usama,Al-Othman, Zeid,Al-Majid, Abdullah,Almansour, Abdulrahman
, p. 3276 - 3280 (2010)
Treatment of N-bromosuccinimide (NBS) with (carboethoxymethylene) triphenylphosphorane (1) in CH2Cl2 followed by the addition of an alcohol in the presence of manganese dioxide under ultrasonic irradiation constitutes a stereoselective one-pot procedure for the preparation of Z-configured α-bromo-α,β-unsaturated esters in good to excellent yield.
Chemoselective construction of substituted conjugated dienes using an olefin cross-metathesis protocol
Funk, Timothy W.,Efskind, Jon,Grubbs, Robert H.
, p. 187 - 190 (2007/10/03)
(Chemical Equation Presented) Various substituted conjugated dienes have been made by olefin cross-metathesis. Using either electronic or steric "protection," one of the olefins of the conjugated diene was deactivated relative to the other for cross-metathesis. The reactions proceed with very high chemoselectivity and, when steric deactivation is used, very high diastereoselectivity.
A highly stereoselective synthesis of (E)-α-bromoacrylates
Tago, Keiko,Kogen, Hiroshi
, p. 8825 - 8831 (2007/10/03)
Novel reagent, methyl bis(2,2,2-trifluoroethoxy)bromophosphonoacetate (5a), was designed and prepared in order to efficiently synthesize (E)-α-bromoacrylates 7, from which widely useful precursors for various C-C bond formations were prepared. Horner-Wadsworth-Emmons (HWE) reaction of various aldehydes with 5a in the presence of t-BuOK and 18-C-6 gave corresponding (E)-α-bromoacrylate derivatives with high stereoselectivity and excellent yield. Using the product (E)-α-bromoacrylate 7s as a key intermediate, we succeeded in developing the most effective route of plaunotol synthesis via Suzuki cross-coupling. (C) 2000 Elsevier Science Ltd.
