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Asymmetric Allylboration of Ketones Catalyzed by Chiral Diols

2006; American Chemical Society; Volume: 128; Issue: 39 Linguagem: Inglês

10.1021/ja0651308

1943-2984

Sha Lou, Philip N. Moquist, Scott E. Schaus,

Synthetic Organic Chemistry Methods

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.