A General Protocol toward Oxindoles Bearing C3‐Allylic Quaternary Stereocenter via Domino Reaction: A Concise Synthesis of Heterocycle‐Fused Indoline Alkaloids

Abstract

Comprehensive SummaryAn efficiently catalytic method toward the synthesis of indolin‐2‐ones featuring an allylic derived C3‐quaternary stereocenter via an intramolecular Heck cyclization/Suzuki coupling of N‐substituted‐N‐(2‐bromophenyl)acrylamides and organoboron reagents was successfully developed by using a 1,3‐bis(2,6‐diisopropylphenyl)acenaphthoimidazol‐2‐ylidene (AnIPr)‐ligated oxazoline palladacycle. It enabled a very broad substrate scope tolerating different functional groups, electronic properties and steric bulkiness. Notably, it revealed a great potential to build diverse heterocycle‐fused indoline alkaloids via the same intermediate 3‐allyl‐1,3‐dimethylindolin‐2‐ one.