• Bulletin of the Korean Chemical Society
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• v.32 no.6
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• pp.1808-1846
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• 2011

From 1975 to 2011, for thirty six years, the author and his collaborators have developed a variety of reducing and hydroborating agents, and applied them to organic synthesis, which involves the 1,2-reduction of ${\alpha}$,${\beta}$-unsaturated carbonyl compounds, stereoselective reduction of cycloalkanones, regioselective ring-opening of epoxides, partial reduction of carboxylic acid derivatives to aldehydes, regioselective addition to carbon-carbon multiple bonds, etc. by utilizing metal hydrides and the newly-devised the Meerwein-Ponndorf-Verley (MPV) type reagents. Such developments provide a new synthetic methodology making possible valuable selective reductions and hydroborations, not practical previously.

• Bulletin of the Korean Chemical Society
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• v.16 no.1
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• pp.37-42
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• 1995

Reactions of alkenes and alkynes with the recently discovered isopinocampheylhaloborane-methyl sulfide (IpcBHX·SMe2, X=Cl, Br, I) were investigated in detail in order to establish their usefulness as hydroborating agents. The reagents readily hydroborated alkenes at 50 ℃ and alkynes at 25 ℃ with excellent regioselectivity in placing the boron atom exclusively at the less hindered carbon atom. Especially, the selectivity achieved by the iodo derivative reaches essentially 100%. In addition to that, IpcBHX·SMe2 was applied to the reduction of cyclic ketones to examine its stereoselectivity. The halogen substituent in these reagents plays an important role in the stereoselective reduction. The stereoselectivity increased dramatically with increasing steric size of the substituent. Finally, the iodo derivative achieved highly stereoselective reduction, such selectivity being comparable to that previously achieved with trialkylborohydrides.