Diastereoselective synthesis of enantiomerically pure syn- or anti-β-alkyl γ-alkoxyesters by addition of organometallic compounds to α-alkoxy isopropylidene alkylidenemalonates
- 1 January 1989
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Chemical Communications
- No. 1,p. 31-33
- https://doi.org/10.1039/c39890000031
Abstract
The stereochemistry of the conjugate additions 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.Keywords
This publication has 0 references indexed in Scilit: