Reductions with tris(pentafluorophenyl)borane, B(C6F5)3, are rapidly being developed due to the versatile and robust nature of the complex and its compatibility with a variety of functional groups. While most transformations tend to decrease molecular complexity, we have developed a B(C6F5)3-catalyzed method for the selective conversion of unsaturated linear carbohydrates to complex cyclopentane and cyclopropane scaffolds using tertiary silane reductants. Key to the stereospecific intramolecular C–C bond formation are the sila-tetrahydrofuran cation intermediates that arise from chemoselective C–O bond activation. Complex chiral synthons are obtained in a single pot in up to &gt;98:2 d.r. and 95% yield.

Diastereoselective B(C6F5)3-catalyzed reductive carbocyclization of unsaturated carbohydrates

253rd National Meeting (2017)

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