Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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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)
  • Published : 1994.06.20
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Abstract

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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