Journal of Integrative Natural Science (통합자연과학논문집)
- Volume 2 Issue 3
- /
- Pages.185-189
- /
- 2009
- /
- 3022-8883(pISSN)
Selective Reduction of Orgainc Compounds with Al-Fluorodiisobutylalane
- Cha, Jin Soon (Department of Chemistry, Yeungnam University) ;
- Park, Seung Jin (Department of Chemistry, Yeungnam University)
- Received : 2009.08.26
- Accepted : 2009.09.21
- Published : 2009.09.30
Abstract
The new MPV-type reagent, Al-fluorodiisobutylalane (DIBAF), has been prepared and their 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 unique applicability in organic synthesis. In general, the reagent is extremely mild, showing only reactivity toward aldehydes, ketones, and epoxides. The reagent achives a clean 1,2-reduction of enals to the corresponding allylic alcohols in a 100% purity, but shows no reactivity toward enones. The reagent also shows an excellent regioselective cleavage of substituted epoxides. In addition, DIBAF produces the thermodynamically more stable alcohol epimer in high stereoselectivity in the reduction of cyclic ketones.