A Sequential Transition Metal and Organocatalytic Approach to the Enantioselective Synthesis of C2-Spiroindoline
Pooja Sah1, Aakash Kumar Gond1, Gaurav Saini1
1Department of Chemistry, Indian Institute of Science Education and Research Bhopal, Bhopal Bypass Road, Bhauri, Bhopal, 462066, MP, India.
Abstract:
We report herein an organocatalyzed enantioselective spirocyclization strategy to access valuable C2-spiroindoline scaffolds bearing a quaternary stereocenter via an aza-Michael addition reaction, wherein the acid additive plays the role of dual functionality. The substrates for this key step were put together by an exo-selective, Pd-catalyzed γ-arylation of silyldienol ethers of the corresponding cyclohexenones. A close alliance between a low catalyst loading and a slow reaction rate yields C2-spiroindolines with good enantioselectivity.
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