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

Language(s) - English

Resource type - Journals

eISSN - 1521-3757

pISSN - 0044-8249

DOI - 10.1002/ange.201909158

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