期刊
ACS CATALYSIS
卷 11, 期 3, 页码 1361-1367出版社
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.0c05225
关键词
allenic ketone; bifunctional phosphine; [4+2] annulation; quaternary stereogenic centers; dielectrophilic; dinucleophilic
资金
- National Natural Science Foundation of China [21672158]
- Singapore National Research Foundation (NRF) [R-143-000-A15-281]
- National University of Singapore [R-143-000-695-114, C-141-000-092-001]
In this study, we introduced a new type of allenic ketone as a dielectrophilic C4 synthon in phosphine-mediated reactions, enabling a highly enantioselective [4 + 2] annulation. This strategy allowed for the facile creation of spirocyclic bisindoline structures containing two contiguous quaternary stereogenic centers. Synthetic manipulations of the [4 + 2] annulation product led to concise total synthesis of (-)-folicanthine.
We introduced a type of allenic ketone as a dielectrophilic C4 synthon in phosphine-mediated reactions. The high electrophilicity of the advanced intermediates created upon phosphine activation empowered the utilization of 3,3'-bis-oxindoles as a two-carbon reaction partner in a highly enantioselective [4 + 2] annulation, allowing for facile creation of spirocyclic bisindoline structures containing two contiguous quaternary stereogenic centers. Synthetic manipulations of the [4 + 2] annulation product led to concise total synthesis of (-)-folicanthine.
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