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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
Kinetic Resolution of Spiroindolines through Ir-Catalyzed Asymmetric Allylative Ring-Opening Reaction
Jianhui Qiao1, Wenju Chang1, Wenxuan Zhao1
1State Key Laboratory of Coordination Chemistry, Jiangsu Key Laboratory of Advanced Organic Materials, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210023, China.
Abstract:
Kinetic resolution of racemic spiroindolines with s factors of ≤15200 has been developed to access enantiomerically enriched indole-annulated medium-sized lactams and spiroindolines through Ir-catalyzed asymmetric allylative ring-opening reaction. Density functional theory calculations support the idea that the accurate discrimination of two spiroindoline enantiomers by (η3-allyl)-iridium(III) species and the perfect central-to-axial chirality conversion during C-C bond fragmentation ensure the stereoselective formation of two contiguous stereogenic centers and one axis in the medium-sized lactams.
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