Palladium‐Catalyzed Asymmetric [4+3] Cyclization of Trimethylenemethane: Regio‐, Diastereo‐, and Enantioselective Construction of Benzofuro[3,2‐ b ]azepine Skeletons | Zendy

Liu YangZi | Zendy; Wang Zhongao | Zendy; Huang Zesheng | Zendy; Zheng Xing | Zendy; Yang WuLin | Zendy; Deng WeiPing | Zendy

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Palladium‐Catalyzed Asymmetric [4+3] Cyclization of Trimethylenemethane: Regio‐, Diastereo‐, and Enantioselective Construction of Benzofuro[3,2‐ b ]azepine Skeletons

Author(s) -

Liu YangZi,

Wang Zhongao,

Huang Zesheng,

Zheng Xing,

Yang WuLin,

Deng WeiPing

Publication year - 2020

Publication title -

angewandte chemie international edition

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 5.831

H-Index - 550

eISSN - 1521-3773

pISSN - 1433-7851

DOI - 10.1002/anie.201909158

Subject(s) - trimethylenemethane , azepine , enantioselective synthesis , palladium , catalysis , chemistry , benzofuran , stereochemistry , medicinal chemistry , combinatorial chemistry , organic chemistry , cycloaddition

The palladium‐catalyzed asymmetric [4+3] cyclization of trimethylenemethane donors with benzofuran‐derived azadienes furnishes chiral benzofuro[3,2‐ b ]azepine frameworks in high yields (up to 98 %) with exclusive regioselectivities and excellent stereoselectivities (up to >20:1 d.r., >99 % ee ). This catalytic asymmetric [4+3] cyclization of Pd‐trimethylenemethane can enrich the arsenal of Pd‐TMM reactions in organic synthesis. In addition, this strategy provides an alternative approach to chiral azepines by a transition‐metal‐catalyzed asymmetric [4+3] cyclization.

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