Asymmetric allylboration of ketones catalyzed by chiral diols |
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| Authors: | Lou Sha Moquist Philip N Schaus Scott E |
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| Institution: | 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. |
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| Abstract: | 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. |
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