General Asymmetric Hydrogenation of α-Branched Aromatic Ketones Catalyzed by TolBINAP/DMAPEN−Ruthenium(II) Complex

A catalyst system consisting of RuCl2[(S)-tolbinap][(R)-dmapen] and t-C4H9OK in 2-propanol effects asymmetric hydrogenation of arylglyoxal dialkylacetals to give the α-hydroxy acetals in up to 98% ee. Hydrogenation of racemic α-amidopropiophenones under dynamic kinetic resolution predominantly gives...

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Veröffentlicht in:Organic letters 2007-03, Vol.9 (5), p.939-941
Hauptverfasser: Arai, Noriyoshi, Ooka, Hirohito, Azuma, Keita, Yabuuchi, Toshio, Kurono, Nobuhito, Inoue, Tsutomu, Ohkuma, Takeshi
Format: Artikel
Sprache:eng
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Zusammenfassung:A catalyst system consisting of RuCl2[(S)-tolbinap][(R)-dmapen] and t-C4H9OK in 2-propanol effects asymmetric hydrogenation of arylglyoxal dialkylacetals to give the α-hydroxy acetals in up to 98% ee. Hydrogenation of racemic α-amidopropiophenones under dynamic kinetic resolution predominantly gives the syn alcohols in up to 99% ee and >98% de, while the reaction of racemic bezoin methyl ether gives the anti alcohols in excellent stereoselectivity.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol070125+