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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 16, Number 1
BKCSDE 16(1)
January 20, 1995

Title	Isopinocampheylhaloborane-Methyl Sulfide as Hydroborating and Stereoselective Reducing Agent
Author	Jin Soon Cha*, Soo Jin Min, Jong Mi Kim, Oh Oun Kwon, Eun Ju Kim
Keywords
Abstract	Reactions of alkenes and alkynes with the recently discovered isopinocampheylhaloborane-methyl sulfide (IpcBHX·SMe2, X=Cl, Br, I) were investigated in detail in order to establish their usefulness as hydroborating agents. The reagents readily hydroborated alkenes at 50 ℃ and alkynes at 25 ℃ with excellent regioselectivity in placing the boron atom exclusively at the less hindered carbon atom. Especially, the selectivity achieved by the iodo derivative reaches essentially 100%. In addition to that, IpcBHX· SMe2 was applied to the reduction of cyclic ketones to examine its stereoselectivity. The halogen substituent in these reagents 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.
Page	37 - 42
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