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Asymmetric Intramolecular Amination Catalyzed with Cp*Ir-SPDO via Nitrene Transfer for Synthesis of Spiro-Quaternary Indolinone.
Wei, Shi-Qiang; Li, Zi-Hao; Wang, Shuang-Hu; Chen, Hua; Wang, Xiao-Yu; Gu, Yun-Zhou; Zhang, Ye; Wang, Hong; Ding, Tong-Mei; Zhang, Shu-Yu; Tu, Yong-Qiang.
Affiliation
  • Wei SQ; School of Chemistry and Chemical Engineering, Frontier Scientific Center of Transformative Molecules, Shanghai Key Laboratory of Chiral Drugs and Engineering, Shanghai Jiao Tong University, Shanghai, Minhang 200240, China.
  • Li ZH; School of Chemistry and Chemical Engineering, Frontier Scientific Center of Transformative Molecules, Shanghai Key Laboratory of Chiral Drugs and Engineering, Shanghai Jiao Tong University, Shanghai, Minhang 200240, China.
  • Wang SH; School of Chemistry and Chemical Engineering, Frontier Scientific Center of Transformative Molecules, Shanghai Key Laboratory of Chiral Drugs and Engineering, Shanghai Jiao Tong University, Shanghai, Minhang 200240, China.
  • Chen H; College of Pharmaceutical Science and Collaborative Innovation Cent of Yangtze River Delta Region Green Pharmaceuticals, Zhejiang University of Technology, Hangzhou 310014, China.
  • Wang XY; School of Chemistry and Chemical Engineering, Frontier Scientific Center of Transformative Molecules, Shanghai Key Laboratory of Chiral Drugs and Engineering, Shanghai Jiao Tong University, Shanghai, Minhang 200240, China.
  • Gu YZ; School of Chemistry and Chemical Engineering, Frontier Scientific Center of Transformative Molecules, Shanghai Key Laboratory of Chiral Drugs and Engineering, Shanghai Jiao Tong University, Shanghai, Minhang 200240, China.
  • Zhang Y; School of Chemistry and Chemical Engineering, Frontier Scientific Center of Transformative Molecules, Shanghai Key Laboratory of Chiral Drugs and Engineering, Shanghai Jiao Tong University, Shanghai, Minhang 200240, China.
  • Wang H; College of Pharmaceutical Science and Collaborative Innovation Cent of Yangtze River Delta Region Green Pharmaceuticals, Zhejiang University of Technology, Hangzhou 310014, China.
  • Ding TM; School of Chemistry and Chemical Engineering, Frontier Scientific Center of Transformative Molecules, Shanghai Key Laboratory of Chiral Drugs and Engineering, Shanghai Jiao Tong University, Shanghai, Minhang 200240, China.
  • Zhang SY; School of Chemistry and Chemical Engineering, Frontier Scientific Center of Transformative Molecules, Shanghai Key Laboratory of Chiral Drugs and Engineering, Shanghai Jiao Tong University, Shanghai, Minhang 200240, China.
  • Tu YQ; School of Chemistry and Chemical Engineering, Frontier Scientific Center of Transformative Molecules, Shanghai Key Laboratory of Chiral Drugs and Engineering, Shanghai Jiao Tong University, Shanghai, Minhang 200240, China.
J Am Chem Soc ; 146(28): 18841-18847, 2024 Jul 17.
Article in En | MEDLINE | ID: mdl-38975938
ABSTRACT
An asymmetric intramolecular spiro-amination to high steric hindering α-C-H bond of 1,3-dicarbonyl via nitrene transfer using inactive aryl azides has been carried out by developing a novel Cp*Ir(III)-SPDO (spiro-pyrrolidine oxazoline) catalyst, thereby enabling the first successful construction of structurally rigid spiro-quaternary indolinone cores with moderate to high yields and excellent enantioselectivities. DFT computations support the presence of double bridging H-F bonds between [SbF6]- and both the ligand and substrate, which favors the plane-differentiation of the enol π-bond for nitrenoid attacking. These findings open up numerous opportunities for the development of new asymmetric nitrene transfer systems.
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Full text: 1 Collection: 01-internacional Database: MEDLINE Language: En Journal: J Am Chem Soc Year: 2024 Document type: Article
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PubMed Links
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Full text: 1 Collection: 01-internacional Database: MEDLINE Language: En Journal: J Am Chem Soc Year: 2024 Document type: Article