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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 31, Number 4
BKCSDE 31(4)
April 20, 2010 

Selective Reduction of Organic Compounds with Al-Methanesulfonyldiisobutylalane
Jin Soon Cha*, Minyeong Noh
Al-Methanesulfonyldiisobutylalane, Selective reduction, Organic functional groups, MPV type
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 慣,棺-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.
840 - 844
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