Stereodivergent Construction of Contiguous Quaternary Carbon Centers Enabled by Asymmetric Catalysis
Jiyou Huo, Xiuhuan Li, Qianhu Chen, Pengpeng Gao, Yi Hou, Pan Lei, Huanhuan Zou, Jiahang Yan, Xiaolong Wan, Weiqing Xie
Abstract
Herein, we report the discovery of the catalytic asymmetric conjugated addition of allylstannanes to indol-2-ones promoted by Ni(II)/chiral N,N′ -dioxide. This method enables the stereodivergent construction of contiguous quaternary carbon centers (CQCCs), which can be readily achieved by a suitable combination of a chiral catalyst with stereospecific allylstannanes. This protocol allows for a unified access to all stereoisomers of 3,3-disubstituted oxindoles with CQCCs in good to excellent enantioselectivities and diastereoselectivities.
Topics & Concepts
CatalysisQuaternary carbonConjugated systemStereospecificityChemistryEnantioselective synthesisCarbon fibersCombinatorial chemistryAsymmetric carbonOrganic chemistryComputer scienceOptically activePolymerAlgorithmComposite numberAsymmetric Synthesis and CatalysisAsymmetric Hydrogenation and CatalysisSynthetic Organic Chemistry Methods