Thirty Six Years of Research on the Selective Reduction and Hydroboration

Abstract

thirty six years, the author and his collaborators have developed a variety of reducing and hydroborating agents, and applied them to organic synthesis, which involves the 1,2-reduction of α,β-unsaturated carbonyl compounds, stereoselective reduction of cycloalkanones, regioselective ring-opening of epoxides, partial reduction of carboxylic acid derivatives to aldehydes, regioselective addition to carbon-carbon multiple bonds, etc. by utilizing metal hydrides and the newly-devised the Meerwein-Ponndorf-Verley (MPV) type reagents. Such developments provide a new synthetic methodology making possible valuable selective reductions and hydroborations, not practical previously.

Biocatalytic reduction of carboxylic acids

“…A number of examples for chemical reductions of carboxylic acids to the corresponding aldehydes were reported in the literature (Fig. 1B) [4–6]. However, the routinely used strategy is based on the overreduction to the alcohol and subsequent selective re‐oxidation to the aldehyde with the aid of pyridinium chlorochromate, Dess‐Martin periodinane, TEMPO or via Swern oxidation [7].…”