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Palladium-Catalyzed Intermolecular Asymmetric Dearomative Annulation of Phenols with Vinyl Cyclopropanes.
Chu, Wen-Dao; Liang, Tian-Tian; Ni, Hao; Dong, Zhi-Hong; Shao, Zhihui; Liu, Yong; He, Cheng-Yu; Bai, Ruopeng; Liu, Quan-Zhong.
Affiliation
  • Chu WD; Chemical Synthesis and Pollution Control Key Laboratory of Sichuan Province, College of Chemistry and Chemical Engineering, China West Normal University, No. 1, Shida Road, Nanchong 637002, P. R. China.
  • Liang TT; Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education, School of Chemical Science and Technology, Yunnan Provincial Center for Research & Development of Natural Products, State Key Laboratory for Conservation and Utilization of Bio-Resources in Yunnan, Yunnan Universi
  • Ni H; Chemical Synthesis and Pollution Control Key Laboratory of Sichuan Province, College of Chemistry and Chemical Engineering, China West Normal University, No. 1, Shida Road, Nanchong 637002, P. R. China.
  • Dong ZH; School of Chemistry and Chemical Engineering, Chongqing Key Laboratory of Theoretical and Computational Chemistry, Chongqing University, Chongqing 401331, P. R. China.
  • Shao Z; Chemical Synthesis and Pollution Control Key Laboratory of Sichuan Province, College of Chemistry and Chemical Engineering, China West Normal University, No. 1, Shida Road, Nanchong 637002, P. R. China.
  • Liu Y; Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education, School of Chemical Science and Technology, Yunnan Provincial Center for Research & Development of Natural Products, State Key Laboratory for Conservation and Utilization of Bio-Resources in Yunnan, Yunnan Universi
  • He CY; Chemical Synthesis and Pollution Control Key Laboratory of Sichuan Province, College of Chemistry and Chemical Engineering, China West Normal University, No. 1, Shida Road, Nanchong 637002, P. R. China.
  • Bai R; Chemical Synthesis and Pollution Control Key Laboratory of Sichuan Province, College of Chemistry and Chemical Engineering, China West Normal University, No. 1, Shida Road, Nanchong 637002, P. R. China.
  • Liu QZ; School of Chemistry and Chemical Engineering, Chongqing Key Laboratory of Theoretical and Computational Chemistry, Chongqing University, Chongqing 401331, P. R. China.
Org Lett ; 24(27): 4865-4870, 2022 07 15.
Article in En | MEDLINE | ID: mdl-35775729
Herein, we report the Pd(0)-catalyzed intermolecular asymmetric dearomative [3 + 2] annulation of phenols with vinyl cyclopropanes via in situ generated ortho-quinone methide intermediates. A series of highly functionalized spiro-[5,6] bicycles which bear three contiguous stereogenic centers including one all-carbon quaternary were obtained with excellent stereoselectivities. Density functional theory (DFT) calculations indicate that the reactions were controlled by thermodynamics.
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Full text: 1 Collection: 01-internacional Database: MEDLINE Main subject: Palladium / Cyclopropanes Language: En Journal: Org Lett Journal subject: BIOQUIMICA Year: 2022 Document type: Article Country of publication: United States
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Full text: 1 Collection: 01-internacional Database: MEDLINE Main subject: Palladium / Cyclopropanes Language: En Journal: Org Lett Journal subject: BIOQUIMICA Year: 2022 Document type: Article Country of publication: United States