title: Enantioselective synthesis of (E)-δ-silyl-anti-homoallylic alcohols via an enantiodivergent hydroboration-crotylboration reaction of a racemic allenylsilane.
abstract: 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.
authors.affiliation: Department of Chemistry, Scripps Florida, Jupiter, Florida 33458, United States.
authors.forename: Ming
authors.initials: M
authors.lastname: Chen
authors.forename: William R
authors.initials: WR
authors.lastname: Roush
mesh_terms: D000438:Alcohols / Q000138:chemical synthesis* / Q000737:chemistry; D000447:Aldehydes / Q000737:chemistry; D000466:Alkadienes / Q000737:chemistry*; D001896:Boron Compounds / Q000737:chemistry*; D015394:Molecular Structure; D012821:Silanes / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000438:Alcohols; D000447:Aldehydes; D000466:Alkadienes; D001896:Boron Compounds; D012821:Silanes; C025947:propadiene