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Pd-Catalyzed Enantioselective Tandem C-C Bond Activation/Cacchi Reaction between Cyclobutanones and o-Ethynylanilines.
Yang, Wan-Chun; Chen, Xiao-Bing; Song, Kun-Long; Wu, Bin; Gan, Wan-Er; Zheng, Zhan-Jiang; Cao, Jian; Xu, Li-Wen.
Affiliation
  • Yang WC; Key Laboratory of Organosilicon Chemistry and Material Technology of Ministry of Education, and Key Laboratory of Organosilicon Material Technology of Zhejiang Province, Hangzhou Normal University, No. 2318, Yuhangtang Road, Hangzhou 311121, P.R. China.
  • Chen XB; Key Laboratory of Organosilicon Chemistry and Material Technology of Ministry of Education, and Key Laboratory of Organosilicon Material Technology of Zhejiang Province, Hangzhou Normal University, No. 2318, Yuhangtang Road, Hangzhou 311121, P.R. China.
  • Song KL; Key Laboratory of Organosilicon Chemistry and Material Technology of Ministry of Education, and Key Laboratory of Organosilicon Material Technology of Zhejiang Province, Hangzhou Normal University, No. 2318, Yuhangtang Road, Hangzhou 311121, P.R. China.
  • Wu B; Key Laboratory of Organosilicon Chemistry and Material Technology of Ministry of Education, and Key Laboratory of Organosilicon Material Technology of Zhejiang Province, Hangzhou Normal University, No. 2318, Yuhangtang Road, Hangzhou 311121, P.R. China.
  • Gan WE; Key Laboratory of Organosilicon Chemistry and Material Technology of Ministry of Education, and Key Laboratory of Organosilicon Material Technology of Zhejiang Province, Hangzhou Normal University, No. 2318, Yuhangtang Road, Hangzhou 311121, P.R. China.
  • Zheng ZJ; Key Laboratory of Organosilicon Chemistry and Material Technology of Ministry of Education, and Key Laboratory of Organosilicon Material Technology of Zhejiang Province, Hangzhou Normal University, No. 2318, Yuhangtang Road, Hangzhou 311121, P.R. China.
  • Cao J; Key Laboratory of Organosilicon Chemistry and Material Technology of Ministry of Education, and Key Laboratory of Organosilicon Material Technology of Zhejiang Province, Hangzhou Normal University, No. 2318, Yuhangtang Road, Hangzhou 311121, P.R. China.
  • Xu LW; Key Laboratory of Organosilicon Chemistry and Material Technology of Ministry of Education, and Key Laboratory of Organosilicon Material Technology of Zhejiang Province, Hangzhou Normal University, No. 2318, Yuhangtang Road, Hangzhou 311121, P.R. China.
Org Lett ; 23(4): 1309-1314, 2021 Feb 19.
Article in En | MEDLINE | ID: mdl-33539100
ABSTRACT
A palladium-catalyzed asymmetric tandem C-C bond activation/Cacchi reaction between cyclobutanones and o-ethynylanilines was reported. The transient chiral σ-alkylpalladium species generated via enantioselective C(sp3)-C(sp2) bond activation of cyclobutanones promotes cyclization of o-ethynylanilines, leading to one-carbon-tethered chiral indanone-substituted indoles. Two C-C bonds and one C-N bond are created with concomitant formation of an all-carbon quaternary stereocenter. Furthermore, a chiral C2-aryl axis can be created in 2,3-disubstituted indole moiety, leading to indanone-substituted indoles with both central and axial stereogenic elements.
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Full text: 1 Collection: 01-internacional Database: MEDLINE Language: En Journal: Org Lett Journal subject: BIOQUIMICA Year: 2021 Document type: Article
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Full text: 1 Collection: 01-internacional Database: MEDLINE Language: En Journal: Org Lett Journal subject: BIOQUIMICA Year: 2021 Document type: Article