121644-20-0Relevant academic research and scientific papers
Diastereoselective Synthesis of Enantiomerically Pure syn- or anti-β-Alkyl γ-Alkoxyesters by Addition of Organometallyc Compounds to α-Alkoxy Isopropylidene Alkylidenemalonates
Larcheveque, Marc,Tamagnan, Gilles,Petit, Yves
, p. 31 - 33 (2007/10/02)
The stereochemistry of the conjugate addition of organometallic compounds R2M (M=Li or Mg) to O-protected α-hydroxy alkylidene isopropylidenemalonates is highly dependent on the nature of the protecting group; in the case of the MEM group, syn-compounds were obtained almost exclusively with Grignard compounds whereas the use of a non-chelating protecting group such as ButPh2Si afforded nearly pure anti-compounds with organolithium compounds in the presence of 12-crown-4.
