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　alpha-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.　(C)　2022　Science　China　Press.　Published　by　Elsevier　B.V.　and　Science　China　Press.　All　rights　reserved.