text: Alkoxyaluminium and closely related hydride reagents reduce a wide variety of functional groups, often with good selectivity. This section, organized by functional group, covers the most common or synthetically useful methods for alkoxyaluminium hydride reduction of organic compounds.
  Many selective reductions of carbonyl compounds can be effected by taking advantage of the unique reactivity profiles of metal alkoxylaluminium hydrides. For instance, lithium tri-tert-butoxy)aluminium hydride (LTBA) reduces aldehydes and ketones selectively in the presence of esters, with which it reacts extremely slowly.
  α,β-Unsaturated ketones may be reduced selectively in a 1,2 or 1,4 sense by a judicious choice of reducing agent. Use of relatively unhindered lithium trimethoxyaluminium hydride results in nearly quantitative direct addition to the carbonyl group (Eq. ()). On the other hand, use of the bulky reagent LTBA leads to a high yield of the conjugate addition product (Eq. ()).
  Ether cleavage is difficult to accomplish with most hydride reagents. However, debenzylation of benzyl aryl ethers may be accomplished with SMEAH. This protocol is a useful alternative to methods requiring acid or hydrogenolysis (e.g., Pd/C and hydrogen gas).
  Epoxides are generally attacked by alkoxyaluminium hydrides at the less substituted position. A nearby hydroxyl group may facilitate intramolecular delivery of the hydride reagent, allowing for selective opening of 1,2-disubstituted epoxides at the position closer to the hydroxyl group. The configuration at the untouched epoxide carbon is preserved.
  Unsaturated carbonyl compounds may be reduced either to saturated or unsaturated alcohols by alkoxyaluminium hydride reagents. Addition of an unsaturated aldehyde to a solution of Red-Al afforded the saturated alcohol; inverse addition yielded the unsaturated alcohol product.
  Alkenes undergo hydroalumination in the presence of some alkoxyaluminium hydrides. In a related application, NaAlH(OCHCHOCH) (sodium bis(methoxyethoxy) aluminium dihydride, SMEAH or Red-Al) reacts with zirconocene dichloride to afford zirconocene chloride hydride (Schwartz's reagent). Alkenes undergo hydrozirconation in the presence of this reagent, affording functionalized products after quenching with an electrophile.
  Functional groups containing heteroatoms other than oxygen may also be reduced to the corresponding hydrocarbons in the presence of an alkoxyaluminium hydride reagent. Primary alkyl halides undergo reduction to the corresponding alkanes in the presence of NaAlH(OH)(OCHCHOCH). Secondary halides are less reactive, but afford alkanes in reasonable yield.
  Sulfoxides are reduced to the corresponding sulfides in good yield in the presence of SMEAH. 
  Imines are reduced by metal alkoxyaluminium hydrides to the corresponding amines. In the example below, use of the exo amine forms with high diastereoselectivity. The selectivity of hydride reduction in this case is higher than that of catalytic hydrogenation.