Asymmetric Allylboration of Ketones Catalyzed by Chiral Diols

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...

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Veröffentlicht in:Journal of the American Chemical Society 2006-10, Vol.128 (39), p.12660-12661
Hauptverfasser: Lou, Sha, Moquist, Philip N, Schaus, Scott E
Format: Artikel
Sprache:eng
Schlagworte:
Alcohols - chemistry
Allyl Compounds - chemistry
Boranes - chemical synthesis
Catalysis
Chemistry
Exact sciences and technology
General and physical chemistry
Ketones - chemistry
Models, Molecular
Stereoisomerism
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Zusammenfassung: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.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja0651308