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, NaAlH2(OCH2CH2OCH3)2 (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)(OCH2CH2OCH3)2. 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. Experimental conditions and procedure Preparation of hydride reagents Alkoxyaluminium hydrides are typically prepared by treatment of lithium aluminium hydride with the corresponding alcohol. Hydrogen evolution indicates the formation of alkoxyaluminium hydride products. Hindered hydrides such as lithium tri-(tert-butoxy)aluminium hydride (LTBA) are stable for long periods of time under inert atmosphere, but lithium trimethoxyaluminium hydride (LTMA) undergoes disproportionation and should be used immediately after preparation. Pure, solid Red-Al is stable for several hours under inert atmosphere and is available commercially as a 70%-solution in toluene under the trade name Vitride or Synhydrid. Reduction conditions Reduction may typically be carried out in a round-bottom flask equipped with a drying-tube-capped reflux condenser, a mercury-sealed mechanical stirrer, a thermometer, a nitrogen inlet, and an additional funnel with a pressure-equalizing side arm. The most common solvents used are tetrahydrofuran and diethyl ether. Whatever solvent is used should be anhydrous and pure. Alkoxyaluminium hydrides should be kept as dry as possible and represent a significant fire hazard, particularly when an