4.7 Article

Chiral bisformamides as effective organocatalysts for the asymmetric one-pot, three-component strecker reaction

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JOURNAL OF ORGANIC CHEMISTRY
卷 72, 期 20, 页码 7715-7719

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AMER CHEMICAL SOC
DOI: 10.1021/jo701307f

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[GRAPHICS] C-2-symmetric chiral bisformamides have been shown to catalyze the asymmetric one-pot, three-component Strecker reaction, which produced the alpha-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.

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