Bulletin of the Korean Chemical Society

  • 제15권6호
  • /
  • Pages.478-483
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  • 1994
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  • 0253-2964(pISSN)
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  • 1229-5949(eISSN)
대한화학회 (Korean Chemical Society)
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Thexylhaloborane-Methyl Sulfide as Hydroborating and Stereoselective Reducing Agent

  • Cha Jin Soon (Department of Chemistry, Yeungnam University) ;
  • Min Soo Jin (Department of Chemistry, Yeungnam University) ;
  • Kim, Jong Mi (Department of Chemistry, Yeungnam University)
  • 발행 : 1994.06.20
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초록

Reactions of alkenes and alkynes with thexylhaloborane-methyl sulfide (ThxBHX${\cdot}$SMe$_2$, X= Cl, Br, I) were investigated in detail in order to elucidate the effect of halogen substituent in thexylborane and hence establish their usefulness as hydroborating agent. The reagents readily hydroborated alkenes at $50^{circ}C$and alkynes at $25^{circ}C$ in exceptional regioselectivity. Especially, the selectivity achieved by the bromo and iodo derivative reaches essentially 100%. In addition to that, $ThxBHX{\cdot}SMe_2$ was applied to the reduction of cyclic ketones to examine its stereoselectivity. The halogen substituent in thexylborane 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.

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참고문헌

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피인용 문헌

  1. Studies on the Properties of Thexylboronic Acid and Its Derivatives vol.26, pp.2, 1994, https://doi.org/10.5012/bkcs.2005.26.2.292
  2. Thirty Six Years of Research on the Selective Reduction and Hydroboration vol.32, pp.6, 1994, https://doi.org/10.5012/bkcs.2011.32.6.1808