Lithium tri-tert-butoxyaluminum hydride, LTBA
A highly efficient in situ generation of the Schwartz reagent provides a convenient method for the reduction of amides to aldehydes and the regioselective hydrozirconation-iodination of alkynes and alkenes. These single-step processes proceed in very short reaction time, show excellent functional group compatibility, and use inexpensive and long-storage stable reducing reagents.
Y. Zhao, V. Snieckus, Org. Lett., 2014, 16, 390-393.
In a sequential one-pot process for the conversion of sterically demanding N,N-diisopropylamides to aldehydes, amides are activated with EtOTf to form imidates, which are reduced with LiAlH(OR)3 [R = t-Bu, Et] to give aldehydes by hydrolysis of the resulting hemiaminals. The non-nucleophilic base 2,6-DTBMP remarkably improves reaction efficiency. The reaction tolerates various reducible functional groups, including aldehyde and ketone.
P. Xiao, Z. Tang, K. Wang, H. Chen, Q. Guo, Y. Chu, L. Gao, Z. Song, J. Org. Chem., 2018, 83, 1687-1700.