期刊
ACS CATALYSIS
卷 8, 期 11, 页码 10180-10189出版社
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.8b02157
关键词
asymmetric catalysis; sequential reaction; gold catalysis; trispirocyclic framework; hetero-Diels-Alder Reaction
资金
- National Natural Science Foundation of China [21532006, 21472187, 21702203]
- Strategic Priority Research Program of the Chinese Academy of Sciences [XDB17000000]
Chiral spirooxindole is the core structure of a large number of natural and unnatural products with biological activities. However, the construction of trispirocyclic oxindoles remains challenging because of the difficulty in the assembly, the complex skeleton, and control of the stereoselectivities of the multiple quaternary stereocenters. Herein, we present the organic base/Au(I)-catalyzed sequential asymmetric 1,2-addition/cascade hydroamination/HDA/deisobutene reactions for the elaboration of various trispirocyclic N,O-ketal tethered oxindoles and bisoxindoles in excellent optical purities (91-99% ee). Key to the success of this methodology is Au(I)-catalyzed hetero-Diels Alder reactions utilizing N-Boc-iminooxindoles as the heterodienes.
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