☆ 4.8 Article

Silane-Controlled Diastereoselectivity in the Tris(pentafluorophenyl)borane-Catalyzed Reduction of α-Diketones to Silyl-Protected 1,2-Diols

ORGANIC LETTERS (2010)

期刊

ORGANIC LETTERS

卷 12, 期 2, 页码 376-379

出版社

AMER CHEMICAL SOC

DOI: 10.1021/ol902451h

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Chemistry, Organic

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NSERC
Inorganic Chemistry Exchange (ICE)

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Reagent

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B(C6F5)(3)-catalyzed bis(hydrosilylation) of alpha-diketones can give high diastereomeric excess of either meso/anti (small silanes and disilane reagents) or dl/syn (bulky silanes) silyl-protected 1,2-diols. This easily tuned diastereoselectivity is rationalized based on the classic Felkin-Anh model applied to a mechanism relying on Si-H abstraction by the electrophilic borane reagent.

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