Herein　we　report　a　catalytic　asymmetric　dearomatization　reaction　of　electron-deficient　heteroarenes　with　alpha-substituted　isocyanoacetates　through　an　interrupted　Barton-Zard　reaction.　A　range　of　optically　active　pyrrolo[3,4-b]indole　derivatives　was　obtained　in　good　yields　(up　to　97　%)　with　high　stereoselectivities　(up　to　＞20:1　dr　and　97　%　ee),　using　a　catalytic　system　consisting　of　a　cinchona-derived　amino-phosphine　and　silver　oxide.　This　reaction　features　wide　substrate　scope　and　mild　conditions,　and　provides　a　new　strategy　for　developing　asymmetric　dearomatization　reactions.