Enantioselective Addition of Boronates to o‑Quinone Methides Catalyzed by Chiral Biphenols

Enantioselective Addition of Boronates to o‑Quinone Methides Catalyzed by Chiral Biphenols

Chiral biphenols were found to catalyze the enantioselective asymmetric addition of aryl- or alkenylboronates to o-quinone methides. Substituted 2-styryl phenols were obtained in good yields (up to 95%) with high enantiomeric ratios (up to 98:2) in the presence of 10 mol % 3,3′-Br2-BINOL. A two-step...

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Veröffentlicht in:Journal of the American Chemical Society 2012-12, Vol.134 (49), p.19965-19968
Hauptverfasser: Luan, Yi, Schaus, Scott E
Format: Artikel
Sprache:eng
Schlagworte:
Benzoquinones - chemical synthesis
Benzoquinones - chemistry
Boronic Acids - chemistry
Catalysis
Indolequinones - chemistry
Molecular Structure
Phenols - chemical synthesis
Phenols - chemistry
Stereoisomerism
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Zusammenfassung:Chiral biphenols were found to catalyze the enantioselective asymmetric addition of aryl- or alkenylboronates to o-quinone methides. Substituted 2-styryl phenols were obtained in good yields (up to 95%) with high enantiomeric ratios (up to 98:2) in the presence of 10 mol % 3,3′-Br2-BINOL. A two-step synthesis of (S)-4-methoxydalbergione in good yield and selectivity was achieved.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja309076g