Enantioselective Synthesis of Indole-Annulated Medium-Sized Rings
Lin Huang1, Li-Xin Dai1, Shu-Li You1,2
1State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences , 345 Lingling Lu, Shanghai 200032, China.
Abstract:
Asymmetric synthesis of indole-annulated medium-sized-ring compounds is developed through an iridium-catalyzed allylic dearomatization/retro-Mannich/hydrolysis cascade reaction. The reaction features mild conditions and a broad substrate scope. Under the optimal conditions, various seven-, eight-, or nine-membered-ring compounds can be afforded in good to excellent yields and excellent enantioselectivity. The proposed mechanism is supported by capturing the dearomatized intermediate through in situ reduction.
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