title: Enantioconvergent hydroboration of a racemic allene: enantioselective synthesis of (E)-δ-stannyl-anti-homoallylic alcohols via aldehyde crotylboration.
abstract: The enantioconvergent hydroboration of racemic allenylstannane (±)-1 with ((d)Ipc)(2)BH converts both enantiomers of (±)-1 into the enantioenriched crotylborane (S)-E-3. Subsequent crotylboration of aldehydes with (S)-E-3 provides (E)-stannyl-homoallylic alcohols 5 in good yields and with excellent enantioselectivity.
authors: Department of Chemistry, Scripps Florida, Jupiter, Florida 33458, United States.
authors: Ming
authors: M
authors: Chen
authors: William R
authors: WR
authors: Roush
mesh_terms: D000438:Alcohols / Q000138:chemical synthesis* / Q000737:chemistry; D000447:Aldehydes / Q000138:chemical synthesis / Q000737:chemistry*; D000498:Allyl Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D001880:Boranes / Q000138:chemical synthesis / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000438:Alcohols; D000447:Aldehydes; D000498:Allyl Compounds; D001880:Boranes