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The enantioselective hydroboration of racemic allenylsilane (±)-4 with ((d)Ipc)2BH proceeds via enantiodivergent pathways to give vinylborane 11 and crotylborane intermediate (S)-E-5. Subsequent crotylboration of aldehyde substrates with (S)-E-5 at -78 °C provides (E)-δ-silyl-anti-homoallylic alcohols in 71-89% yield and with 93-96% ee.

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Enantioselective Synthesis of (<i>E</i>)-δ-Silyl-<i>anti</i>-homoallylic Alcohols via an Enantiodivergent Hydroboration-Crotylboration Reaction of a Racemic Allenylsilane

Enantioselective Synthesis of (E)-δ-Silyl-anti-homoallylic Alcohols via an Enantiodivergent Hydroboration-Crotylboration Reaction of a Racemic Allenylsilane