• Bulletin of the Korean Chemical Society
• /
• v.27 no.5
• /
• pp.667-671
• /
• 2006

The new MPV-type reagents, B-acetoxydiisopinocampheylborane ($Ipc _2$BOAc) and B-trifluoroacetoxydiisopinocampheylborane $(Ipc _2BO _2CCF _3)$, 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 $Ipc _2BO _2CCF _3$ appears to be stronger than that of $Ipc _2$BOAc, presumably due to the acidity increase by the electron-withdrawing fluorine-substituent. Both reagents show an excellent selectivity in 1,2-reduction of $\alpha,\beta$-unsaturatedcarbonyl compounds and in competitive reduction between structurally different carbonyl compounds. In addition, $Ipc _2BO _2CCF _3$ shows interesting features in the stereoreduction of cyclic ketones.

• Bulletin of the Korean Chemical Society
• /
• v.30 no.7
• /
• pp.1658-1660
• /
• 2009

• Bulletin of the Korean Chemical Society
• /
• v.17 no.8
• /
• pp.725-729
• /
• 1996

Reaction of carbonyl compounds with B-alkoxydiisopinocampheylborane (Ipc2BOR, R=H, Et, i-Pr, t-Bu) was investigated in detail in order to establish their usefulness as selective reducing agents. The reagents were extremely mild and reduced only aldehydes effectively under mild conditions. The reagents also reduced α,β-unsaturated aldehydes to the corresponding allylic alcohols without any detectable 1,4-reduction. Furthermore, aldehydes can be reduced in the presence of epoxides and acid chlorides. Consequently, the selective reduction of aldehyde groups in the presence of keto and all other functional groups has been realized with these reagents.

• Bulletin of the Korean Chemical Society
• /
• v.25 no.5
• /
• pp.603-604
• /
• 2004

• Bulletin of the Korean Chemical Society
• /
• v.23 no.8
• /
• pp.1051-1052
• /
• 2002

• Journal of the Korean Chemical Society
• /
• v.15 no.3
• /
• pp.117-120
• /
• 1971

Possibility of two phase reduction of carbonyl compounds to the corresponding alcohols was studied. Thus the 0.5 M ether solutions of the representative carbonyl compounds were treated with alkaline stabilized sodium borohydride aqueous solution at room temperature. Butyraldehyde was reduced rapidly within one hr., whereas other aldehydes tested; heptaldehyde, benzaldehyde, and 1-naphthaldehyde were reduced in 6-12 hr. 2-Heptanone was reduced much slowly; 87% in 48 hr., however, acetophenone was reduced moderately; 92% in 12 hr. and cycloalkanones were reduced rapidly (cyclohexanone in 0.5 hr., and cyclopentanone in 3-6 hr.).

• Bulletin of the Korean Chemical Society
• /
• v.31 no.10
• /
• pp.2961-2966
• /
• 2010

Reduction of carbonyl compounds such as aldehydes, ketones, $\alpha,\beta$-unsaturated enals and enones, $\alpha$-diketones and acyloins was carried out readily with $NaBH_3CN$ in the presence of wet $SiO_2$ as a neutral media. The reactions were performed at solvent-free conditions in oil bath (70 - $80^{\circ}C$) or under microwave irradiation (240 W) to give the product alcohols in high to excellent yields. Regioselective 1,2-reduction of conjugated carbonyl compounds took place in a perfect selectivity without any side product formation.

• Bulletin of the Korean Chemical Society
• /
• v.24 no.11
• /
• pp.1664-1670
• /
• 2003

$NaBH_4$ with catalytic amounts of $MoCl_5$ can readily reduce a variety of carbonyl compounds such as aldehydes, ketones, acyloins, ${\alpha}$-diketones and conjugated enones to their corresponding alcohols in good to excellent yields. Reduction reactions were performed under aprotic condition in $CH_3CN$ at room temperature or reflux. In addition, the chemoselective reduction of aldehydes over ketones was accomplished successfully with this reducing system.

• Journal of Integrative Natural Science
• /
• v.1 no.3
• /
• pp.192-194
• /
• 2008

A series of non-free hydride reducing systems containing boron or aluminum atom, which possess no metal-hydride bond but an available hydrogen at a branched ${\beta}$-position, has been applied to the selective reduction (chemo--, regio-, and stereoselective reduction) of organic compounds. The systems, comprised of diisopinocampheylborane and diisobutylalane derivatives, exhibited almost perfect selectivities in the reduction of aldehydes and ketones. The characteristics features of this systems leading to a perfect transformation have been depicted in this report, especially in the 1) Reduction of ${\alpha}$,${\beta}$-Unsaturated Carbonyl Compounds to Allylic Alcohols via 1,2-Reduction, 2) Chemoselective Reduction between Structurally Different Carbonyl Compounds, and 3) Stereoselective Reduction of Cyclic Ketones.

• Bulletin of the Korean Chemical Society
• /
• v.24 no.4
• /
• pp.453-459
• /
• 2003

(Pyridine)(tetrahydroborato)zinc complex, $[Zn(BH_4)_2(py)]$, as a stable white solid, was prepared quantitatively by complexation of an equimolar amount of zinc tetrahydroborate and pyridine at room temperature. This reagent can easily reduce variety of carbonyl compounds such as aldehydes, ketones, acyloins, α-diketones and a, β-unsaturated carbonyl compounds to their corresponding alcohols in good to excellent yields. Reduction reactions were performed in ether or THF at room temperature or under reflux conditions. In addition, the chemoselective reduction of aldehydes over ketones was accomplished successfully with this reducing agent.