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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 15, Number 6
BKCSDE 15(6)
June 20, 1994 

Thexylhaloborane-Methyl Sulfide as Hydroborating and Stereoselective Reducing Agent
Jin Soon Cha*, Soo Jin Min, Jong Mi Kim
Reactions of alkenes and alkynes with thexylhaloborane-methyl sulfide (ThxBHX·SMe2, 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℃ and alkynes at 25℃ in exceptional regioselectivity. Especially, the selectivity achieved by the bromo and iodo derivative reaches essentially 100%. In addition to that, ThxBHX·SMe2 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.
478 - 483
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