Bulletin of the Korean Chemical Society

  • 제32권1호
  • /
  • Pages.219-224
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  • 2011
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  • 0253-2964(pISSN)
  • /
  • 1229-5949(eISSN)
대한화학회 (Korean Chemical Society)
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Selective Reduction of Organic Compounds with Al-Trifluoromethanesulfonyldiisobutylalane. Comparison of Its Reactivity with Al-Methanesulfonyldiisobutylalane

  • 투고 : 2010.11.01
  • 심사 : 2010.11.15
  • 발행 : 2011.01.20
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초록

The new MPV type reagent, Al-trifluoromethanesulfonyldiisobutylalane ($DIBAO_3SCF_3$), has been prepared and its reducing characteristics in the reduction of selected organic compounds containing representative functional groups have been examined, and compared its reactivity with that of Al-methanesulfonyldiisobutylalane ($DIBAO_3SCH_3$) in order to understand the fluorine-substituent effect on its reactivity. In general, the reactivity of $DIBAO_3SCF_3$ appears to be much higher than that of $DIBAO_3SCH_3$, apparently due to the acidity increase by the electron-withdrawing fluorine-substituent. The reagent reduced aldehydes and ketones readily, but showed a perfect selectivity in the reduction of $\alpha,\beta$-unsaturated aldehydes and ketones to produce the corresponding allylic alcohols in an absolutely 100% purity. In addition, the reagent achieved the regioselective cleavage of phenyl- or/and alkyl-substituted epoxides to the less substituted alcohols in a perfect regioselectivity. Moreover, the reagent also showed an high stereoselectivity in the reduction of substituted cycloalkanones to produce the thermodynamically more stable alcohol epimers exclusively.

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참고문헌

  1. Cha, J. S.; Yi, J. E. J. Incl. Phenom. Macro. 2009, 65, 15. https://doi.org/10.1007/s10847-009-9629-3
  2. Cha, J. S.; Park, S. J. Bull. Korean Chem. Soc. 2009, 30, 2823. https://doi.org/10.5012/bkcs.2009.30.11.2823
  3. Cha, J. S.; Park, S. J. Bull. Korean Chem. Soc. 2010, 31, 2135 https://doi.org/10.5012/bkcs.2010.31.8.2135
  4. Cha, J. S.; Noh, M. Bull. Korean Chem. Soc. 2010, 31, 840. https://doi.org/10.5012/bkcs.2010.31.04.840
  5. Brown, H. C.; Yoon, N, M. Chem. Commun. 1968, 1549.
  6. Hutchins, R. O.; Taffer, I. M.; Burgoyne, W. J. Org. Chem. 1981, 46, 5214. https://doi.org/10.1021/jo00338a031
  7. Yoon, N. M.; Kim, K. E. J. Org. Chem. 1987, 52, 5564. https://doi.org/10.1021/jo00234a011
  8. Cha, J. S.; Park, J. H. Bull. Korean Chem. Soc. 2002, 23, 1377. https://doi.org/10.5012/bkcs.2002.23.10.1377
  9. Cha, J. S.; Park, S. J.; Yu, S. J.; Kim, S. K.; Kwon, O. O. Bull. Korean Chem. Soc. 2008, 29, 301. https://doi.org/10.5012/bkcs.2008.29.2.301
  10. Cha, J. S. Org. Proc. Res. Devel. 2006, 10, 1032. https://doi.org/10.1021/op068002c
  11. Bull. Korean Chem. Soc. 2007, 28, 2162. https://doi.org/10.5012/bkcs.2007.28.12.2162
  12. Cha, J. S.; Kwon, O. O. J. Org. Chem. 1997, 62, 3019. https://doi.org/10.1021/jo970083a

피인용 문헌

  1. Thirty Six Years of Research on the Selective Reduction and Hydroboration vol.32, pp.6, 2011, https://doi.org/10.5012/bkcs.2011.32.6.1808
  2. ChemInform Abstract: Selective Reduction of Organic Compounds with Al-Trifluoromethanesulfonyldiisobutylalane. Comparison of Its Reactivity with Al-Methanesulfonyldiisobutylalane. vol.42, pp.22, 2011, https://doi.org/10.1002/chin.201122033
  3. Regiospecific Ring-Opening of Unsymmetrical Epoxides to the Corresponding Less Substituted Alcohols by Newly-Devised Meerwein-Ponndorf-Verley Type Reagents vol.5, pp.2, 2012, https://doi.org/10.13160/ricns.2012.5.2.091
  4. Relative Reactivity of Various Al-substituted-dialkylalans in Reduction of Carbonyl Compounds: A Theoretical Study on Substituent Effect vol.34, pp.8, 2013, https://doi.org/10.5012/bkcs.2013.34.8.2335
  5. The Stereoselective Reductions of Ketones to the Most Thermodynamically Stable Alcohols Using Lithium and Hydrated Salts of Common Transition Metals vol.80, pp.16, 2015, https://doi.org/10.1021/acs.joc.5b01232