Lithium aluminium hydride: chemoselective reduction with

A few papers have reported the use of various aluminium-based reducing agents in phosphine synthesis. Lithium aluminium hydride reduction of phosphine oxide precursors provides a route to new 2-phosphinomethyl-1/7-pyrroles and diisobutylaluminium hydride (DIBAL) has been found to be an excellent reagent for the reduction of phosphinites, phosphinates and chlorophosphines. 2-Chloroethylphosphine (CICH2CH2PH2) has been prepared for the first time by a chemoselective reduction of diethyl 2-chloroethylphosphonate with dichloroalane (HAICI2), prepared in situ from LiAlH4 and AlCls. A patent has described the use of metallic aluminium... 

Lithium aluminium hydride modified with some chiral 1,2-aminodiols, for example (106), gives enantiomeric excesses of up to 82% in the reduction of aromatic ketones," and lithium tris[(3-ethyl-3-pentyl)oxy]aluminium hydride has been introduced as a chemoselective reagent (98—100%) for the reduction of aldehydes in the presence of ketones." Finally, the reagents AlCL-EtSH and AlBrs-EtSH have found further application in the cleavage of esters and lactones. 

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