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Rh(III)-Catalyzed Relay Double Carbenoid Insertion and Diannulation of Sulfoximine Benzamides with α-Diazo Carbonyl Compounds: Access to Furo[2,3-c]isochromenes.
Yang, Chen; Chen, Chen; Li, Shunfan; He, Xinwei; Zuo, Youpeng; Hu, Wangcheng; Zhou, Tongtong; Wang, Jian; Shang, Yongjia.
Affiliation
  • Yang C; Key Laboratory of Functional Molecular Solids, Ministry of Education, Anhui Laboratory of Molecule-Based Materials (State Key Laboratory Cultivation Base), College of Chemistry and Materials Science, Anhui Normal University, Wuhu 241002, P. R. China.
  • Chen C; Key Laboratory of Functional Molecular Solids, Ministry of Education, Anhui Laboratory of Molecule-Based Materials (State Key Laboratory Cultivation Base), College of Chemistry and Materials Science, Anhui Normal University, Wuhu 241002, P. R. China.
  • Li S; Key Laboratory of Functional Molecular Solids, Ministry of Education, Anhui Laboratory of Molecule-Based Materials (State Key Laboratory Cultivation Base), College of Chemistry and Materials Science, Anhui Normal University, Wuhu 241002, P. R. China.
  • He X; Key Laboratory of Functional Molecular Solids, Ministry of Education, Anhui Laboratory of Molecule-Based Materials (State Key Laboratory Cultivation Base), College of Chemistry and Materials Science, Anhui Normal University, Wuhu 241002, P. R. China.
  • Zuo Y; Key Laboratory of Functional Molecular Solids, Ministry of Education, Anhui Laboratory of Molecule-Based Materials (State Key Laboratory Cultivation Base), College of Chemistry and Materials Science, Anhui Normal University, Wuhu 241002, P. R. China.
  • Hu W; Key Laboratory of Functional Molecular Solids, Ministry of Education, Anhui Laboratory of Molecule-Based Materials (State Key Laboratory Cultivation Base), College of Chemistry and Materials Science, Anhui Normal University, Wuhu 241002, P. R. China.
  • Zhou T; Key Laboratory of Functional Molecular Solids, Ministry of Education, Anhui Laboratory of Molecule-Based Materials (State Key Laboratory Cultivation Base), College of Chemistry and Materials Science, Anhui Normal University, Wuhu 241002, P. R. China.
  • Wang J; Key Laboratory of Functional Molecular Solids, Ministry of Education, Anhui Laboratory of Molecule-Based Materials (State Key Laboratory Cultivation Base), College of Chemistry and Materials Science, Anhui Normal University, Wuhu 241002, P. R. China.
  • Shang Y; Key Laboratory of Functional Molecular Solids, Ministry of Education, Anhui Laboratory of Molecule-Based Materials (State Key Laboratory Cultivation Base), College of Chemistry and Materials Science, Anhui Normal University, Wuhu 241002, P. R. China.
Org Lett ; 22(7): 2506-2511, 2020 Apr 03.
Article in En | MEDLINE | ID: mdl-32083484
ABSTRACT
An efficient rhodium-catalyzed construction of furo[2,3-c]isochromene scaffolds through tandem double carbenoid insertion and diannulation of sulfoximine benzamides with α-diazo carbonyl compounds has been developed. Mechanistic studies revealed that the alkyl-rhodium intermediate generated by carbenoid insertion was directly trapped with another molecule of carbene species, followed by subsequent intramolecular cyclization reactions. Sulfoximine was released in situ, featuring a traceless directing fashion. The reactions proceeded smoothly under mild conditions with wide functional group tolerance.
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Full text: 1 Collection: 01-internacional Database: MEDLINE Language: En Journal: Org Lett Journal subject: BIOQUIMICA Year: 2020 Type: Article
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PubMed Links
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Full text: 1 Collection: 01-internacional Database: MEDLINE Language: En Journal: Org Lett Journal subject: BIOQUIMICA Year: 2020 Type: Article