Imidazo[1,2-a]pyridines are present in numerous biologically active compounds as the core structural motif. Herein, we report an asymmetric interrupted Barton-Zard reaction of electron-deficient imidazo[1,2-a]pyridines with α-substituted isocyanoacetates. The reaction enables the dearomatization of 8-nitroimidazo[1,2-a]pyridines and hence offers straightforward access to an array of optically active highly functionalized imidazo[1,2-a]pyridine derivatives that possess three contiguous stereogenic centers in good yields (up to 98%) with high stereoselectivities (>19:1 dr, >99% ee). It is worth noting that the catalytic system consisting of a chiral squaramide and silver oxide displays remarkable reactivity and stereoselectivity, and a gram-scale reaction is compatible with the catalyst loading of 0.5 mol%. In addition, the synthetic potential of this method was showcased by versatile transformations of the product.

咪唑并[1,2- a ]吡啶作为核心结构基序存在于许多生物活性化合物中。在此，我们报道了缺电子咪唑并 [1,2- a ] 吡啶与α取代的异氰基乙酸酯的不对称间断 Barton-Zard 反应。该反应能够使 8-硝基咪唑并 [1,2- a ] 吡啶脱芳构化，因此可以直接获得一系列具有光学活性的高度官能化咪唑并 [1,2- a] 具有三个连续立体中心的吡啶衍生物，收率高（高达 98%），立体选择性高（>19:1 dr，>99% ee）。值得注意的是，由手性角酰胺和氧化银组成的催化体系表现出显着的反应活性和立体选择性，克级反应与 0.5 mol% 的催化剂负载相容。此外，该方法的合成潜力通过产品的多功能转换得到展示。