Di-isobutyl aluminium hydride

Smith, T. P. Reaction of Di-isobutyl Aluminium Hydride with Stannic Chloride. Nature 199, 374 (1963). 

In a related reaction, addition of organocuprates, alkyl zinc bromide or di-isobutyl aluminium hydride to l-trimethylsilylcyclopropenes occurs regio- and stereo-selecti-vely, eg.12) ... 

Reduction of the lactone (351) with di-isobutyl-aluminium hydride gives the related hemi-acetal, cyclodehydration of which gives cis-deoxyalpenigenine (352). Oxidation of this gives the lactone (352) which may be reduced to eis-alp-enigenine (I. Ahmad and V. Sniekus, Canad.J.Chem., 1982, 60, 2678). 

Synthetic work in this area includes a new, stereospecific synthesis of sparteine and a synthesis of isosophoramine. The reduction of quinolizidone (16) by means of lithium aluminium hydride affords, as noted previously, a dimeric product (17), presumably via condensation of the initially formed enamine (18) with the corresponding immonium cation (19). With di-isobutyl aluminium hydride the yield of (17) can be increased to 85%. Analogous reduction of the dilactam (20), prepared by base-catalysed condensation of the bromo-lactam (21) with a-piperidone, gave an intermediate (22), in which the enamine and immonium ion units are present within the same molecule. Intramolecular cyclization of (22), via a transition state derived from the conformation (23), spontaneously gave the... 

Polymeric phosphine oxides in which phosphorus forms part of the polymer backbone have been reduced to the corresponding phosphines in a clean, two-stage, one-pot procedure treatment with oxalyl chloride followed by di-isobutyl-aluminium hydride. This procedure is also applicable to simple phosphine oxides. ... 

In this way trans-hept-2-ene nitrile was prepared in 87% yield from 1-hexyne. Cis-aj8-unsaturated nitriles may be prepared by use of lithium di-isobutylmethyl-aluminium hydride which is prepared from di-isobutyl-aluminium hydride and methyl lithium in monoglyme. This reagent adds trans to alkynes ... 

A further new selective approach to the N -alkylation of polyamines involves the novel reductive cleavage of the C—N bond in cyclic amidines by di-isobutyl aluminium hydride. 

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