Bulletin of the Korean Chemical Society

  • 제17권1호
  • /
  • Pages.50-55
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  • 1996
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  • 0253-2964(pISSN)
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  • 1229-5949(eISSN)
대한화학회 (Korean Chemical Society)
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Selective Reduction of Carbonyl Compounds with Diisopinocampheylhaloboranes

  • 발행 : 19960100
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초록

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.

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참고문헌

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피인용 문헌

  1. ChemInform Abstract: Selective Reduction of Carbonyl Compounds with Diisopinocampheylhaloboranes. vol.27, pp.30, 1996, https://doi.org/10.1002/chin.199630083
  2. (Pyridine)(tetrahydroborato)zinc Complex, [Zn(BH4)2(py)], as a New Stable, Efficient and Chemoselective Reducing Agent for Reduction of Carbonyl Compounds vol.24, pp.4, 1996, https://doi.org/10.5012/bkcs.2003.24.4.453
  3. Selective Reduction of Carbonyl Compounds with B-Phenoxydiisopinocampheylborane: Comparison of Its Reactivity to the Cyclohexoxy Derivative vol.25, pp.12, 1996, https://doi.org/10.5012/bkcs.2004.25.12.1948
  4. Selective Reduction of Carbonyl Compounds with B-Cyclohexoxydiisopinocampheylborane vol.25, pp.5, 1996, https://doi.org/10.5012/bkcs.2004.25.5.603
  5. Wet THF as a Suitable Solvent for a Mild and Convenient Reduction of Carbonyl Compounds with NaBH4 vol.78, pp.2, 1996, https://doi.org/10.1246/bcsj.78.307
  6. Selective Reduction of Carbonyl and Epoxy Compounds Using Aluminum, Boron and Other Metal Reagents. Comparison of Reducing Characteristics between the Meerwein-Ponndorf-Verley Type Reduction and Metal vol.28, pp.12, 1996, https://doi.org/10.5012/bkcs.2007.28.12.2162
  7. Thirty Six Years of Research on the Selective Reduction and Hydroboration vol.32, pp.6, 1996, https://doi.org/10.5012/bkcs.2011.32.6.1808
  8. Regiospecific Ring-Opening of Unsymmetrical Epoxides to the Corresponding Less Substituted Alcohols by Newly-Devised Meerwein-Ponndorf-Verley Type Reagents vol.5, pp.2, 1996, https://doi.org/10.13160/ricns.2012.5.2.091