• Bulletin of the Korean Chemical Society
• /
• v.25 no.11
• /
• pp.1623-1624
• /
• 2004

• Journal of the Korean Chemical Society
• /
• v.26 no.2
• /
• pp.99-106
• /
• 1982

The ketone chromophore of 1-Acetyl-1-methyl-2-cyclopentene (1) was replaced by nitrile, carboxylic acid and acetamide group, and their photochemical reactions were investigated. While the ${\beta},\;{\gamma}$-unsaturated ketone 1 afforded 1,2 ar 1,3-Acyl shift product, these replaced chromophores did not afford any monomeric rearranged products. 1-Cyano-1-methyl-2-cyclohexene also afforded no product anology of the 1,2-acyl shift reaction. The replacement of the ketone chromophore by nitrile, carboxylic acid and carboxamide has greatly altered the photochemistry of ${\beta},\;{\gamma}$-unsaturated ketones.

• Bulletin of the Korean Chemical Society
• /
• v.27 no.6
• /
• pp.857-862
• /
• 2006

The catalytic enantioselective Michael reaction promoted by quaternary ammonium salts from Cinchona alkaloids as a phase-transfer catalyst is described. Treatment of malonates with $\alpha$,$\beta$-unsaturated ketones under mild reaction conditions afforded the corresponding Michael adducts in good yields with good to moderate enantiomeric excesses.

• Bulletin of the Korean Chemical Society
• /
• v.27 no.10
• /
• pp.1674-1676
• /
• 2006

• Bulletin of the Korean Chemical Society
• /
• v.10 no.1
• /
• pp.114-116
• /
• 1989

• Bulletin of the Korean Chemical Society
• /
• v.15 no.12
• /
• pp.1033-1034
• /
• 1994

• Journal of the Korean Chemical Society
• /
• v.19 no.6
• /
• pp.468-470
• /
• 1975

• 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.31 no.4
• /
• pp.840-844
• /
• 2010

The new MPV type reagent, Al-methanesulfonyldiisobutylalane ($DIBAO_3SCH_3$), has been prepared and its 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 high selectivity in organic synthesis. In general, the reagent is extremely mild, showing only reactivity toward aldehydes, ketones and epoxides. The reagent exhibits a unique reducing applicability in organic synthesis. Thus, the reagent can achieve a clean 1,2-reduction of $\alpha,\beta$-unsaturated aldehydes and ketones to produce the corresponding allylic alcohols in 100% purity. In addition, the reagent shows an excellent regioselectivity in the ring-opening reaction of epoxides. Finally, $DIBAO_3SCH_3$ shows a high stereoselectivity in the reduction of cyclic ketones to produce the thermodynamically more stable epimers exclusively.

• Bulletin of the Korean Chemical Society
• /
• v.17 no.1
• /
• pp.50-55
• /
• 1996

Reaction of carbonyl compounds with diisopinocampheylhaloboranes (Ipc2BX,X=Cl, Br, I) was investigated in detail in order to establish their usefulness as selective reducing agents. The reagents reduced aldehydes and ketones to the corresponding alcohols. The reactivities are in the order of Ipc2BCl Ipc2BBr>Ipc2BI.The reagents also reduced ${\alpha}{\beta}-unsaturated$, aldehydes and ketones to the corresponding allylic alcohols without any detectable 1,4-reduction. Especially, the chloro derivative nicely achieved the selective reduction of aldehyde or ketone groups in the presence of many other functional groups. The most remarkable result of this investigation is that aldehydes and ketones can be selectively reduced in the presence of acid chlorides.