Enantioselective Synthesis of Chiral Organosilicon Compounds by Organocatalytic Asymmetric Conjugate Addition of Boronic Acids to β‑Silyl-α,β-Unsaturated Ketones

Herein, we report (R)-3,3′-(3,5-(CF3)2-C6H3)2-BINOL-catalyzed enantioselective conjugate addition of organic boronic acids to β-silyl-α,β-unsaturated ketones, furnishing moderate to excellent yields of the corresponding β-silyl carbonyl compounds with stereogenic centers in excellent enantioselectiv...

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Veröffentlicht in:Journal of organic chemistry 2023-03, Vol.88 (5), p.3254-3265
Hauptverfasser: Wang, Xiao, Chai, Guo-Li, Hou, Ya-Jing, Zhou, Ming-Qian, Chang, Junbiao
Format: Artikel
Sprache:eng
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Zusammenfassung:Herein, we report (R)-3,3′-(3,5-(CF3)2-C6H3)2-BINOL-catalyzed enantioselective conjugate addition of organic boronic acids to β-silyl-α,β-unsaturated ketones, furnishing moderate to excellent yields of the corresponding β-silyl carbonyl compounds with stereogenic centers in excellent enantioselectivities (up to 98% ee). Moreover, the catalytic system features mild reaction conditions, high efficiency, broad substrate scope, and easy scale-up.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.3c00057