114091-85-9Relevant academic research and scientific papers
An efficient synthesis of 2-bromo-3-hydroxy esters by reaction of ketones with ethyl dibromoacetate promoted by samarium diiodide
Concellon, Jose M.,Concellon, Carmen,Diaz, Pamela
, p. 2197 - 2200 (2007/10/03)
A simple and efficient samarium diiodide mediated synthesis of 2-bromo-3-hydroxy esters 1 by the reaction of a variety of ketones 2 with ethyl dibromoacetate (3) is described. The relative configuration of the major diastereoisomer obtained was established by NOESY experiments of the corresponding α,β-epoxy esters 4 prepared from 1. Additionally, a mechanism is proposed to explain the results obtained. Wiley-VCH Verlag GmbH & Co. KGaA, 2006.
α-Bromo-, α-chloro-, and α-trimethylsilyl-zinc ester enolates. New and universal Reformatsky-type Darzens and Peterson reactions
Fuerstner, Alois
, p. C33 - C36 (2007/10/02)
Low temperature reactions of ethyl dihaloacetates with carbonyl compounds in the presence of zinc/silver-graphite give α-halo-β-hydroxyalkanoates, which are readily converted into glycidates by base.Unser the same conditions ethyl(bromo)(trimethylsilyl) acetate with aldehydes and ketones forms α,β-unsaturated esters by a Reformatsky-Peterson reaction combination.
