• Title/Summary/Keyword: Carbonyl compounds

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Selective Reduction of Carbonyl Compounds with Al-Alkoxydiisobutylalanes

  • 차진순;권오운;김종미;전중현;이영수;이형수;조성동
    • Bulletin of the Korean Chemical Society
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    • v.19 no.2
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    • pp.236-242
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    • 1998

  • Reaction of carbonyl compounds with Al-alkoxydiisobutylalane (DIBAOR, R=H, Et, i-Pr, t-Bu) has been investigated in detail so as to establish their usefulness as selective reducing agents in organic synthesis. The reagents appear to be extremely mild and can reduce only aldehydes and ketones effectively under mild conditions. All the other common organic functional groups are not affected by these reagents. The reagents can also reduce α,β-unsaturated aldehydes and ketones to the corresponding allylic alcohols without any detectable 1,4-reduction. Furthermore, the reagents show a highly chemoselective discrimination between aldehyde and ketone, between aldehydes, and between ketones. Even more remarkable is the stereoselective reduction of cyclic ketones to the thermodynamically more stable alcohol epimers.

  • https://doi.org/10.5012/bkcs.1998.19.2.236 인용 PDF