Skip to Content
Merck
  • DIBAL-mediated reductive transformation of trans-dimethyl tartrate acetonide into ε-hydroxy α,β-unsaturated ester and its derivatives.

DIBAL-mediated reductive transformation of trans-dimethyl tartrate acetonide into ε-hydroxy α,β-unsaturated ester and its derivatives.

The Journal of organic chemistry (2011-04-30)
Takashi Tomioka, Yuki Yabe, Tohru Takahashi, Tracy K Simmons
ABSTRACT

Stepwise, selective DIBAL reduction of the acetonide diester derived from tartaric acid followed by the Horner-Emmons reaction effectively provided desymmetrized hydroxy mono-olefination products in a one-pot operation.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Diisobutylaluminum hydride solution, 1.0 M in THF
Sigma-Aldrich
Diisobutylaluminum hydride solution, 1.0 M in toluene
Sigma-Aldrich
Diisobutylaluminum hydride solution, 1.0 M in heptane
Sigma-Aldrich
Diisobutylaluminum hydride solution, 1.0 M in cyclohexane
Sigma-Aldrich
Diisobutylaluminum hydride solution, 1.0 M in methylene chloride
Sigma-Aldrich
Diisobutylaluminum hydride, reagent grade
Sigma-Aldrich
Diisobutylaluminum hydride solution, 1.0 M in hexanes
Sigma-Aldrich
Diisobutylaluminum hydride solution, 25 wt. % in toluene