Selective Reduction of Organic Compounds with Al-Methanesulfonyldiisobutylalane

Bulletin of the Korean chemical society

Jin Soon Cha¹  Minyeong Noh¹ 

关键词: Al-Methanesulfonyldiisobutylalane;    Selective reduction;    Organic functional groups;    MPV typereduction;   

DOI  :  

学科分类：化学（综合）

来源: Korean Chemical Society

【 摘 要 】

The new MPV type reagent, Al-methanesulfonyldiisobutylalane (DIBAO3SCH3), has been prepared and its reducing characteristics in the reduction of selected organic compounds containing representative functional groups have been examined in order to find out a new reducing system with high selectivity in organic synthesis. In general, the reagent is extremely mild, showing only reactivity toward aldehydes, ketones and epoxides. The reagent exhibits a unique reducing applicability in organic synthesis. Thus, the reagent can achieve a clean 1,2-reduction of α,β-unsaturated aldehydes and ketones to produce the corresponding allylic alcohols in 100% purity. In addition, the reagent shows an excellent regioselectivity in the ring-opening reaction of epoxides. Finally, DIBAO3SCH3 shows a high stereoselectivity in the reduction of cyclic ketones to produce the thermodynamically more stable epimers exclusively.

【 授权许可】

Unknown