Lithium trimethoxyaluminohydride

High yields of amines have also been obtained by reduction of amides with an excess of magnesium aluminum hydride (yield 100%) [577], with lithium trimethoxyaluminohydride at 25° (yield 83%) [94] with sodium bis(2-methoxy-ethoxy)aluminum hydride at 80° (yield 84.5%) [544], with alane in tetra-hydrofuran at 0-25° (isolated yields 46-93%) [994, 1117], with sodium boro-hydride and triethoxyoxonium fluoroborates at room temperature (yields 81-94%) [1121], with sodium borohydride in the presence of acetic or trifluoroacetic acid on refluxing (yields 20-92.5%) [1118], with borane in tetrahydrofuran on refluxing (isolated yields 79-84%) [1119], with borane-dimethyl sulflde complex (5 mol) in tetrahydrofuran on refluxing (isolated yields 37-89%) [1064], and by electrolysis in dilute sulfuric acid at 5° using a lead cathode (yields 63-76%) [1120]. 

The stereochemical characteristics of lithium trimethoxyaluminohydride and lithium aluminum hydride in the reduction of cyclic ketones were analyzed by a linear combination of steric strain and product stability control. Qualitative and quantitative explanation of the experimental observations was possible using this approach. ... 

Similar reactions of 9-BBN with alkenes and dienes, followed by carbonyl-ation in the presence of lithium trimethoxyaluminohydride afford the corresponding alcohols or aldehydes (Chart 7.1) [7a]. 

Brown, H. C., Coleman, R. A., Rathke, M. W. 1968. Reaction of carbon monoxide at atmospheric pressure with trialkylboranes in presence of lithium trimethoxyaluminohydride. A convenient procedure for conversion of olefins into aldehydes via hydroboration. J. Am. Chem. Soc. 90 495-501. 

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