Lithium aluminohydride reduction

Schaeffer, G. W., J. S. Roscoe, and A. G. Stewart The Reduction of Iron(III) Chloride with Lithium Aluminohydride and Lithium Borohydride Iron(II) Borohydride. J. Amer. chem. Soc. 78, 729 (1956). 

Unlike with sodium borohydride (see Section 11.01.5.2), pyrrolizin-3-one 2 reacts with lithium aluminohydride mainly as an amide. No conjugate addition occurs, and only the reductive lactam cleavage takes place to give stereoselectively the (Z)-allylie alcohol 77. Similarly, benzo-annulated pyrrolizin-3-one 17 gives the corresponding benzylic alcohol 78. The same reactivity was observed with organometallics such as methyllithium which gives exclusively the tertiary (Z)-allylic alcohol 79 (Scheme 7). 

Treatment of an ethereal solution of 4-oxo-dihydro-l,3-diaza-anthracene (108) with lithium aluminum hydride reportedly resulted in the reduction of only the 1,2-carbon-nitrogen double bond with 4-oxo-l,2,3,4-tetrahydro-l,3-diazaanthracene (109) being the only product isolated.134 Apparently conditions were not sufficiently vigorous for the further reduction of the tautomeric form of 109, or possibly the formation of a complex with the aluminohydride pre-... 

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