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Diastereoselectivity‐Switchable Gold‐Catalyzed Formal [3+2]‐Cycloadditions of N ‐2,2,2‐Trifluoroethylisatin Ketimines with Yne−Enones
Author(s) -
Xiao JunAn,
Cheng XiuLiang,
Peng Hai,
Liang JinShao,
Luo XiaoYan,
Su Wei
Publication year - 2021
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.202100591
Subject(s) - bimetallic strip , diastereomer , catalysis , cycloaddition , chemistry , combinatorial chemistry , formal synthesis , medicinal chemistry , organic chemistry
The unexpected gold‐catalyzed formal [3+2]‐cycloaddition of N ‐2,2,2‐trifluoroethylisatin ketimines with 2‐(1‐Alkynyl)‐2‐alken‐1‐ones is reported. Both diastereomers of the corresponding cycloadducts were formed in moderate to excellent yields with excellent diastereoselectivities by switching the catalytic system from mono‐gold to gold/silver bimetallic catalytic system. The practicality of this protocol is demonstrated by scale‐up reaction and the transformations of the cycloadduct.