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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 32, Number 1
BKCSDE 32(1)
January 20, 2011

Title	Selective Reduction of Organic Compounds with Al-Trifluoromethanesulfonyldiisobutylalane. Comparison of Its Reactivity with Al-Methanesulfonyldiisobutylalane
Author	JIn Soon Cha
Keywords	Al-Trifluoromethanesulfonyldiisobutylalane, Selective reduction, Organic functional groups, MPV type reduction
Abstract	The new MPV type reagent, Al-trifluoromethanesulfonyldiisobutylalane (DIBAO₃SCF₃), has been prepared and its reducing characteristics in the reduction of selected organic compounds containing representative functional groups have been examined, and compared its reactivity with that of Al-methanesulfonyldiisobutylalane (DIBAO₃SCH₃) in order to understand the fluorine-substituent effect on its reactivity. In general, the reactivity of DIBAO₃SCF₃ appears to be much higher than that of DIBAO₃SCH₃, apparently due to the acidity increase by the electron-withdrawing fluorine-substituent. The reagent reduced aldehydes and ketones readily, but showed a perfect selectivity in the reduction of α,β-unsaturated aldehydes and ketones to produce the corresponding allylic alcohols in an absolutely 100% purity. In addition, the reagent achieved the regioselective cleavage of phenyl- or/and alkyl-substituted epoxides to the less substituted alcohols in a perfect regioselectivity. Moreover, the reagent also showed an high stereoselectivity in the reduction of substituted cycloalkanones to produce the thermodynamically more stable alcohol epimers exclusively.
Page	219 - 224
Full Text	PDF

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