Eastwood olefination

What is Eastwood olefination?

Grank and Eastwood were the first to report the Eastwood olefination reaction in 1964. The Eastwood olefination, also known as the Eastwood procedure or Eastwood deoxygenation procedure, is a stereospecific method for producing olefins from vicinal diols through the thermal decomposition of a cyclic orthoformate of the diol in the presence of a catalytic amount of acid (e.g., acetic acid).

Eastwood olefination - general reaction scheme - Eastwood procedure - Eastwood deoxygenation procedure
Eastwood olefination

The cyclic orthoformate can be converted into olefin in high yield by utilizing acetic anhydride as a solvent, which is known as Ando’s modification.

The Eastwood olefination is particularly useful for preparing dideoxy nucleosides and nucleotides, but to avoid N-glycosyl bond cleavage caused by acetic anhydride, hydrous zirconium oxide ZrO2 is used as the catalyst and tributylamine (C4H9)3N is used as the stabilizer for the synthesis of dideoxy thymidine.

The utility of this reaction extends to the synthesis of olefins, dideoxy nucleosides, and nucleotides.