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Summary: J. Am. Chem. SOC.1994,116, 10781-10782 10781
Reversal of Stereoselectivityin the Reduction of
gem-Dichloridesby Tributyltin Hydride and
Tris(trimethylsily1)silane. Synthetic and
Mechanistic Implications
Yitzhak Apeloig* and Moshe Nakash
Department of Chemistry
Technion-Zsrael Institute of Technology
Haifa 32000, Israel
Received July 21, 1994
The most useful reagent for the reduction of alkyl halides is
probably Bu3SnH,* but due to its high toxicity its use for
pharmaceutical applications is generally unacceptable. It was
recently discovered that (Me3Si)sSiH reduces organic halides
in high yields, and due to its low toxicity it is an attractive
altemative to B~3sd-I.~The two reagents have different spatial
shapes: Bu&&I has flexiblechain-typesubstituentswhile (Me3-
Si)sSiH has a spherical and more rigid shape. In this paper we
demonstrate that the different spatial shapes of Bu3SnH and
(Me3Si)jSiH can lead to different, even reversed, product
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