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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

Title	Selective Reduction of Carbonyl Compounds with B-Acetoxy- and B-Trifluoroacetoxydiisopinocampheylboranes
Author	Jin Soon Cha*, Ho Tae Nam, Seung Jin Park, Sang Yong Kwon, Oh Oun Kwon
Keywords	Selective reduction, B-Acetoxydiisopinocampheylborane, B-Trifluoroacetoxydiisopinocampheylborane, MPV type reduction, Carbonyl compounds
Abstract	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.
Page	667 - 671
Full Text	PDF

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