title: Enantiodivergent Hydroboration Reactions of a Racemic Allenylsilane with Diisopinocampheylborane and Curtin-Hammett Controlled Double Asymmetric Crotylboration Reactions of (S)-E-α-phenyldimethylsilyl(ddiisopinocampheyl)-crotylborane.
abstract: The enantiodivergent hydroboration reactions of racemic allenylsilane (±)-4with (dIpc)2BH and subsequent crotylboration of achiral aldehydes with the product crotylborane (S)-E-5at -78 °C provide (E)-δ-silyl-anti-homoallylic alcohols6in 71-89% yield and with 93-96% ee. Intriguingly, mismatched double asymmetric crotylboration reactions of enantioenriched chiral aldehydes20with (S)-E-5proceed under Curtin-Hammett control to giveanti-3-hydroxylcrotylsilanes24as the only products.
authors.affiliation: Department of Chemistry, The Scripps Research Institute, Florida, 130 Scripps Way, Jupiter, FL 33458, USA.
authors.forename: Ming
authors.initials: M
authors.lastname: Chen
authors.forename: William R
authors.initials: WR
authors.lastname: Roush
keywords: Curtin-Hammett control; Enantiodivergent hydroboration; Mismatched double asymmetric crotylboration
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