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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 27, Number 5
BKCSDE 27(5)
May 20, 2006 

Selective Reduction of Carbonyl Compounds with B-Acetoxy- and B-Trifluoroacetoxydiisopinocampheylboranes
Jin Soon Cha*, Ho Tae Nam, Seung Jin Park, Sang Yong Kwon, Oh Oun Kwon
Selective reduction, B-Acetoxydiisopinocampheylborane, B-Trifluoroacetoxydiisopinocampheylborane, MPV type reduction, Carbonyl compounds
The new MPV-type reagents, B-acetoxydiisopinocampheylborane (Ipc2BOAc) and B-trifluoroacetoxydiisopinocampheylborane (Ipc2BO2CCF3), have been prepared and their reducing characteristics in the reduction of carbonyl compound have been examined in order to find out a new reducing system with unique applicability in organic synthesis. In general, the reactivity of Ipc2BO2CCF3 appears to be stronger than that of Ipc2BOAc, presumably due to the acidity increase by the electron-withdrawing fluorine-substituent. Both reagents show an excellent selectivity in 1,2-reduction of α,β-unsaturatedcarbonyl compounds and in competitive reduction between structurally different carbonyl compounds. In addition, Ipc2BO2CCF3 shows interesting features in the stereoreduction of cyclic ketones.
667 - 671
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