Selective reduction of organic compounds with Al-acetoxy- and Al-trifluoroacetoxydiisobutylalane

Autor: Jin Soon Cha, Ja Eun Yi
Rok vydání: 2009
Předmět:
Zdroj: Journal of Inclusion Phenomena and Macrocyclic Chemistry. 65:15-23
ISSN: 1573-1111
0923-0750
DOI: 10.1007/s10847-009-9629-3
Popis: The new MPV-type reagents, Al-acetoxydiisobutylalane (DIBAOAc) and Al-trifluoroacetoxydiisobutylalane (DIBAO2CCF3), have 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 reactivity of DIBAO2CCF3 appears to be much stronger than that of DIBAOAc, presumably due to the acidity increase by the electron-withdrawing fluorine-substituent. Both reagents reduce aldehydes and ketones relatively slowly, but show an excellent selectivity in 1,2-reduction of α,β-unsaturated carbonyl compounds to produce the corresponding allylic alcohols in an absolutely 100% purity. In addition, the reagents achieve the regioselective cleavage of phenyl- or alkyl-substituted epoxides to the less substituted alcohols in an excellent selectivity. Moreover, both reagents show interesting features in the stereoreduction of cyclic ketones. However, these reagents show a very low or/and no reactivity toward most organic functional groups other than carbonyl and epoxy function.
Databáze: OpenAIRE
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