Optically active helicenes and other related helical molecules have received considerable attention due to their high potential as catalysts, liquid crystals and molecular devices. However, efficient enantioselective synthetic method of helicenes, in particular, oxahelicenes, is rather limited. Herein, we report a vanadium catalyzed enantioselective domino oxidative coupling/intramolecular cyclization of polycyclic phenol 1.¹ The vanadium complex (R_a,S)-3 works as a redox² and Lewis acid catalyst³ to promote this sequential reaction to give oxa[9]helicenes 2 in up to 86% yield and 94% ee. The enantiopure 2a (R = H) was readily obtained by a single recrystallization of the product and the absolute configuration of resulting 2a was determined to be (M)-form by X-ray crystallographic analysis. In this presentation, the first regio- and enantioselective oxidative coupling of hydroxycarbazoles⁴ and monocyclic phenols will also be discussed. [References] 1) Sako, M.; Takeuchi, Y.; Tsujihara, T.; Kodera, J.; Kawano, T.; Takizawa, S.; Sasai, H. J. Am. Chem. Soc. 2016, 138, 11481. 2) Kim, H. Y.; Takizawa, S.; Sasai, H.; Oh, K. Org. Lett. 2017, 19, 3867. 3) Takizawa, S.; Arteaga, F. A.; Yoshida, Y.; Kodera, J.; Nagata, Y.; Sasai, H. Dalton Trans. 2013, 42, 11787. 4) Sako, M.; Ichinose, K.; Takizawa, S.; Sasai, H. Chem. Asian J. 2017, 12, 1305.