doi: 10.1021/ja0651308.
Asymmetric allylboration of ketones catalyzed by chiral diols
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- PMID: 17002355
- DOI: 10.1021/ja0651308
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Asymmetric allylboration of ketones catalyzed by chiral diols
J Am Chem Soc.
.
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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