145068-98-0Relevant academic research and scientific papers
3-bromozinc propenyl esters: An experimental and theoretical study of the unique stereocrossover observed in their addition to aromatic and aliphatic aldehydes
Bottoni,Lombardo,Miscione,Pujol Algue,Trombini
, p. 418 - 426 (2008/09/17)
(Chemical Equation Presented) We report the results of a combined experimental and theoretical study on the reaction of 3-bromopropenyl acetate in the presence of zinc with three different aldehydes (i.e., benzaldehyde, 2-methylpropanal, and cyclohexaneca
3-Bromopropenyl esters in organic synthesis: Indium- and zinc-mediated entries to alk-1-ene-3,4-diols
Lombardo, Marco,Morganti, Stefano,Trombini, Claudio
, p. 997 - 1006 (2007/10/03)
Metallic indium and zinc readily add to 3-bromopropenyl acetate (5) and benzoate (6) either in THF or in water, affording the corresponding 3-acyloxyallyl organometallic compounds. Nucleophilic addition to aldehydes opens a route to alk-l-ene-3,4-diols 2 in good to excellent yields. Two synthetic protocols were developed, the former involving indium in THF under Grignard conditions and the latter involving zinc in aqueous ammonium chloride under Barbier conditions. The diastereo-selectivity, under all the conditions examined, mainly depends on the nature of the carbonyl compound; conjugated aldehydes afford syn adducts 2, while unconjugated aldehydes display the opposite anti stereopreference.
3-Chloro-propenyl esters in organic synthesis: A new chromium-catalysed homoaldol reaction
Lombardo, Marco,Morganti, Stefano,Licciulli, Sebastiano,Trombini, Claudio
, p. 43 - 46 (2007/10/03)
Chromium(II) oxidatively adds to 3-halo-propenyl esters affording heterosubstituted allylchromium(III) reagents exploitable in the Nozaki-Hiyama-Kishi reaction. A catalytic cycle based on the Cr(III)-Mn(0) redox couple was applied, affording protected homoaldols as the major products, at 65 °C in acetonitrile as solvent.
Metalated Allylaminosilane: A New, Practical Reagent for the Stereoselective α-Hydroxyallylation of Aldehydes to Erythro-1,2-diol Skeletons
Tamao, Kohei,Nakajo, Eiji,Ito, Yoshihiko
, p. 957 - 958 (2007/10/02)
A zinc reagent derived from allyl(diisopropylamino)dimethylsilane reacts with aldehydes regio- and stereoselectively to form erythro-3-silyl-1-alken-4-ols, which are further transformed into erythro-1-alkene-3,4-diols by hydrogen peroxide oxidation of the
