Catalytic enantioselective α-C–H functionalization of widely available achiral alkyl amines could provide an ideal synthetic approach towards chiral amines. However, the inert nature of the α-C–H of alkyl amines renders their activation as carbanionic nucleophiles for catalytic asymmetric reactions an important yet unmet challenge. Here we describe how N-arylidene-protected alkyl amines could be activated as carbanions for asymmetric conjugate addition and the Mannich reaction. These results represent an intriguing and generally useful approach to the synthesis of chiral α,α-dialkyl amines. More importantly, they highlight the enormous potential of N-arylidene-protected amines as readily available and widely applicable synthons for the asymmetric synthesis of chiral amines.

广泛可用的非手性烷基胺的催化对映选择性 α-C-H 官能团化可以为手性胺提供理想的合成方法。然而，烷基胺的 α-C-H 的惰性性质使其活化为碳离子亲核试剂，用于催化不对称反应，成为一个重要但尚未解决的挑战。在这里，我们描述了如何以碳负离子的形式活化 N-芳基烯保护的烷基胺，用于不对称共轭加成和 Mannich 反应。这些结果代表了合成手性 α，α-二烷基胺的一种有趣且普遍有用的方法。更重要的是，它们强调了 N-芳基保护胺作为手性胺不对称合成的现成且广泛适用的合成子的巨大潜力。