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Asymmetric Catalytic [4+5] Annulation of ortho-Quinone Methides with Vinylethylene Carbonates and its Extension to Stereoselective Tandem Rearrangement.
An, Xian-Tao; Du, Ji-Yuan; Jia, Zhi-Long; Zhang, Qing; Yu, Ke-Yin; Zhang, Yi-Zhou; Zhao, Xian-He; Fang, Ran; Fan, Chun-An.
  • An XT; State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, 222 Tianshui Nanlu, Lanzhou, 730000, China.
  • Du JY; College of Chemistry and Chemical Engineering, Liaocheng University, 1 Hunan Road, Liaocheng, 252059, China.
  • Jia ZL; State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, 222 Tianshui Nanlu, Lanzhou, 730000, China.
  • Zhang Q; State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, 222 Tianshui Nanlu, Lanzhou, 730000, China.
  • Yu KY; State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, 222 Tianshui Nanlu, Lanzhou, 730000, China.
  • Zhang YZ; State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, 222 Tianshui Nanlu, Lanzhou, 730000, China.
  • Zhao XH; State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, 222 Tianshui Nanlu, Lanzhou, 730000, China.
  • Fang R; State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, 222 Tianshui Nanlu, Lanzhou, 730000, China.
  • Fan CA; State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, 222 Tianshui Nanlu, Lanzhou, 730000, China.
Chemistry ; 26(17): 3803-3809, 2020 Mar 23.
Article en En | MEDLINE | ID: mdl-31830333
ABSTRACT
Palladium-catalyzed asymmetric [4+5] annulation of ortho-quinone methides (o-QMs) with substituted vinylethylene carbonates (VECs) is described for the first time, giving a novel enantioselective approach to chiral nine-membered benzoheterocycles. Based on this designed [4+5] annulation, an unprecedented silica gel-promoted tandem rearrangement reaction featuring a unique asymmetric aromatic Claisen rearrangement is explored at room temperature, offering a new method for asymmetric construction of all-carbon quaternary stereocenters embedded in chiral functionalized homoallylic alcohols.
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Texto completo: 1 Banco de datos: MEDLINE Idioma: En Año: 2020 Tipo del documento: Article
Texto completo
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Texto completo: 1 Banco de datos: MEDLINE Idioma: En Año: 2020 Tipo del documento: Article