Metal-catalysed reactions involving ammonia gas are plagued by ammonia’s strong Lewis basicity, which leads to poor chemoselectivity and enantioselectivity. Here we introduce a strategy for preparing chiral α-amino acids directly from ammonia. By the cooperative action of copper complexes and chiral hydrogen-bond donors, enantioselective insertion of carbenes into the N–H bond of ammonia can construct C–N bonds in excellent yield and enantioselectivity. Using this method, we coupled a wide variety of diazoesters with ammonia to produce natural and non-natural chiral α-amino acids, which have a wide range of applications in pharmaceutical and biochemistry research. Our work provides a general method for asymmetric transformations involving ammonia.

涉及氨气的金属催化反应受到氨的强路易斯碱性的困扰，这导致化学选择性和对映选择性差。在这里，我们介绍了一种直接从氨制备手性 α-氨基酸的策略。通过铜配合物和手性氢键供体的协同作用，卡宾对映选择性插入氨的 N-H 键可以以优异的产率和对映选择性构建 C-N 键。使用这种方法，我们将多种重氮酯与氨偶联，产生天然和非天然手性 α-氨基酸，在药物和生物化学研究中具有广泛的应用。我们的工作为涉及氨的不对称转化提供了一种通用方法。