Reductions by Metal Alkoxyaluminum Hydrides. PartII. Carboxylic Acids and Derivatives, Nitrogen Compounds, and Sulfur Compounds

Abstract

In continuation of the previous review on reductions by metal alkoxyaluminum hydrides, this chapter is devoted to reductions of carboxylic acids and their derivatives, open‐chain and heterocyclic nitrogen compounds, and open‐chain and heterocyclic sulfur compounds by alkoxyaluminum hydrides, metal alkoxyaluminum hydrides, and chiral metal alkoxyaluminohydride complexes. Emphasis is placed on the scope, limitations, and the synthetic utility of metal alkoxyaluminum hydrides. Accepted views on reaction mechanisms are mentioned briefly. Discussion of alternative methods of reduction, particularly those using other metal hydrides or complex metal hydrides, is limited to examples of the most important transformations of functional groups; reducing properties of these hydrides and hydride reagents such as borane–dimethyl sulfide, amine boranes, haloboranes, organoboranes, sodium borohydride–pyridine, sodium borohydride–triphenyl borate, sodium borohydride—transition‐metal complexes, potassium triisopropoxyborohydride, and sodium triacyloxyborohydrides have been reported in several papers and reviews. Monographs and reviews summarize reductions with metal alkoxyaluminum hydrides and asymmetric reductions with chiral lithium alkoxyaluminum hydrides and chiral boron reagents.

Unusual pheromone chemistry in the navel orangeworm: novel sex attractants and a behavioral antagonist

“…(3Z,6Z,9Z,12Z,15Z)-3,6,9,12,15-Tricosapentaene (5) and (3Z,6Z,9Z,12Z,15Z)-3,6,9,12,15-pentacosapentaene (6) Commercially available methyl (Z,Z,Z,Z,Z)-5,8,11,14,17-eicosapentaenoate was reduced to the corresponding alcohol with RedAl (Mµlek 1988) (Scheme 1, 5). The alcohol was then converted to bromide, which was coupled to either n-propyl or n-pentyl Grignard catalyzed by copper (Erdik 1984) to give the 5 and 6 pentaenes, respectively.…”

Biocatalytic reduction of carboxylic acids

“…These may, e.g., be esters or amides, acyl halogenides, anhydrides, or carbonates. Typically, complex metal hydrides such as lithium aluminum hydride and sodium borohydride or variants thereof are used in stoichiometric amounts [8, 9]. Catalytic hydrogenations are frequently performed by heterogeneous metal catalysts, however, also homogenous catalytic hydrogenations are strongly emerging [10].…”

Substituted Dibenzodiazocines: Rapid Synthesis and Photochemical Properties

“…Thus, by exposing the organic phase after the work-up to air in the presence of Cu 2+ , the yield of 1a could be maximized. We also tried to moderate the reactivity of the LiAlH 4 by replacing some of the hydrogen atoms with other ligands like alkoxy groups. , In addition, alternative complex hydrides were tested, which have been reported for the dimerization of nitroarenes to the analogous azobenzenes. − The results are summarized in Table .…”