Journal of the Chemical Society. Chemical communications p. 31 - 33 (1989)
Update date:2022-08-02
Topics:
Larcheveque, Marc
Tamagnan, Gilles
Petit, Yves
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.
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