Chiral Bisformamides as Effective Organocatalysts for the Asymmetric One-Pot, Three-Component Strecker Reaction

C 2 -symmetric chiral bisformamides have been shown to catalyze the asymmetric one-pot, three-component Strecker reaction, which produced the α-amino nitriles in excellent yields (up to 99%) with good enantioselectivities (up to 86% ee). Optically pure products could be obtained after a single recry...

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Veröffentlicht in:Journal of organic chemistry 2007-09, Vol.72 (20), p.7715-7719
Hauptverfasser: Wen, Yuehong, Xiong, Yan, Chang, Lu, Huang, Jinglun, Liu, Xiaohua, Feng, Xiaoming
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Sprache:eng
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Zusammenfassung:C 2 -symmetric chiral bisformamides have been shown to catalyze the asymmetric one-pot, three-component Strecker reaction, which produced the α-amino nitriles in excellent yields (up to 99%) with good enantioselectivities (up to 86% ee). Optically pure products could be obtained after a single recrystallization. A possible transition state (TS 1) has been proposed to explain the origin of asymmetric inductivity and reactivity according to the geometry of catalyst 2a optimized at the B3LYP/6-31G(d) level and the absolute configuration of product 4a.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo701307f