Asymmetric allylboration of ketones catalyzed by chiral diols.
Chiral BINOL-derived diols catalyze the enantioselective asymmetric allylboration of ketones. The reaction requires 15 mol % of 3,3'-Br2-BINOL as the catalyst and allyldiisopropoxyborane as the nucleophile. The reaction products are obtained in good yields (76-93%) and high enantiomeric ratios (95:5-99.5:0.5). High diastereoselectivities (dr >/= 98:2) and enantioselectivities (er >/= 98:2) are obtained in the reactions of acetophenone with crotyldiisopropoxyboranes.
Lou
Sha
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Department of Chemistry, BU Center for Chemical Methodology and Library Development, Life Science and Engineering Building, Boston University, 24 Cummington Street, Boston, MA 02215, USA.
Moquist
Philip N
PN
Schaus
Scott E
SE
D000438:Alcohols / Q000737:chemistry*; D000498:Allyl Compounds / Q000737:chemistry*; D001880:Boranes / Q000138:chemical synthesis*; D002384:Catalysis; D007659:Ketones / Q000737:chemistry*; D008958:Models, Molecular; D013237:Stereoisomerism
D000438:Alcohols; D000498:Allyl Compounds; D001880:Boranes; D007659:Ketones