Selective Reduction of Carbonyl Compounds with B-Acetoxy- and B-Trifluoroacetoxydiisopinocampheylboranes

Bulletin of the Korean chemical society

Oh Oun Kwon¹  Ho Tae Nam¹  Seung Jin Park¹  Jin Soon Cha¹  Sang Yong Kwon¹ 

关键词: Selective reduction;    B-Acetoxydiisopinocampheylborane;    B-Trifluoroacetoxydiisopinocampheylborane;    MPV type reduction;    Carbonyl compounds;   

DOI  :  

学科分类：化学（综合）

来源: Korean Chemical Society

【 摘 要 】

The new MPV-type reagents, B-acetoxydiisopinocampheylborane (Ipc₂BOAc) and B-trifluoroacetoxydiisopinocampheylborane (Ipc₂BO₂CCF₃), have been prepared and their reducing characteristics in the reduction of carbonyl compound have been examined in order to find out a new reducing system with unique applicability in organic synthesis. In general, the reactivity of Ipc₂BO₂CCF₃ appears to be stronger than that of Ipc2BOAc, presumably due to the acidity increase by the electron-withdrawing fluorine-substituent. Both reagents show an excellent selectivity in 1,2-reduction of �?,�?-unsaturatedcarbonyl compounds and in competitive reduction between structurally different carbonyl compounds. In addition, Ipc₂BO₂CCF₃ shows interesting features in the stereoreduction of cyclic ketones.

【 授权许可】

Unknown