DIBAL-H, Diisobutylaluminium hydride
Recent Literature

Treatment of 3-[(alkoxycarbonyl)alkyl]-substituted conjugated cycloalkenones
with diisobutylaluminum hydride at -78 °C followed by acid quenching
furnishes spiro ethers, whereas the corresponding 3-(carboxyalkyl)-substituted
cycloalkenones generate spiro lactones upon reaction with sodium borohydride
at 30 °C followed by acid quenching.
M.-C. P. Yeh, Y.-C. Lee, T.-C. Young,
Synthesis, 2006, 3621-3624.

Esters and Weinreb amides undergo reduction to the corresponding aldehydes
using DIBAL-H followed by same pot conversion to terminal alkynes utilizing the
Bestmann-Ohira reagent in good to excellent yields.
H. D Dickson, S. C. Smith, K. W. Hinkle, Tetrahedron Lett., 2004,
45, 5597-5599.

R. S. Porto, M. L. A. A. Vasconcellos, E. Ventura, F. Coelho, Synthesis, 2005, 2297-2306.

Vinylaluminum reagents prepared from the reaction of commercially available
DIBAL-H and a terminal alkyne can be used directly without purification in
catalytic asymmetric allylic alkylation reactions with allylic phosphates in the
presence of a readily available chiral N-heterocyclic carbene (NHC)
complex and a commercially available and air stable Cu salt.
Y. Lee, K. Akiyama, D. G. Gillingham, M. Kevin Brown, A. H. Hoveyda, J. Am. Chem. Soc., 2008,
130, 446-447.

Many tertiary phosphine oxides undergo considerable reduction at ambient
temperature with diisobutylaluminum hydride and then stall due to inhibition.
Source of this inhibition is tetraisobutyldialuminoxane (TIBAO), which builds up
as the reaction proceeds and selectively coordinates the TPO starting material.
Several strategies have been found to circumvent this inhibition.
C. A. Busacca, R. Raju, N. Grinberg, N. Haddad, P. James-Jones, H. Lee, J. C.
Lorenz, A. Saha, C. H. Senanayake, J. Org. Chem., 2008,
73, 1524-1531.
