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In the previous communication, we reported that Bcyclohexoxydiisopinocampheylborane, a new alicyclic derivative of diisopinocampheylborane, is one of the mildest reducing agents, which can reduce only an aldehyde function among the reducible general organic functionalities. The reagent readily reduces a variety of aldehydes at room temperature, but very slowly at 0 C. It is evident that the reduction proceeds via a cyclic boatilike transition state being considered as a Meerwein-Ponndorf-Verley (MPV) type reaction. In the mechanistic point of view, the key step of such reactions must be the coordination of boron atom of reagent to the carbonyl oxygen of substrate. We believe that the reactivity of diisopino-campheylborane derivatives correlates to their Lewis acidity and steric requirement: stronger the coordination, faster the reduction rate. Accordingly, we decided to examine the reducing characteristics of Bphenoxydiisopinocampheylborane (Ipc2BOPh), an aromatic derivative, and compare its reactivity to that of the cyclohexoxy derivative (Ipc2BOChex), in hopes of better understanding the nature of reagent and exploring its role in organic synthesis.

Selective Reduction of Carbonyl Compounds with B-Phenoxydiisopinocampheylborane: Comparison of Its Reactivity to the Cyclohexoxy Derivative