Highly Enantioselective Titanium-Catalyzed Cyanation of Imines at Room Temperature

A highly active and enantioselective titanium-catalyzed cyanation of imines at room temperature is described. The catalyst used is a partially hydrolyzed titanium alkoxide (PHTA) precatalyst together with a readily available N-salicyl-β-aminoalcohol ligand. Up to 98% ee was obtained with quantitativ...

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Veröffentlicht in:Organic letters 2010-01, Vol.12 (2), p.264-267
Hauptverfasser: Seayad, Abdul Majeed, Ramalingam, Balamurugan, Yoshinaga, Kazuhiko, Nagata, Takushi, Chai, Christina L. L
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Sprache:eng
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Zusammenfassung:A highly active and enantioselective titanium-catalyzed cyanation of imines at room temperature is described. The catalyst used is a partially hydrolyzed titanium alkoxide (PHTA) precatalyst together with a readily available N-salicyl-β-aminoalcohol ligand. Up to 98% ee was obtained with quantitative yields in 15 min of reaction time using 5 mol % of the catalyst. Various N-protecting groups such as benzyl, benzhydryl, Boc, and PMP are tolerated.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol902540h