期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 61, 期 17, 页码 -出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202200880
关键词
Auto-Tandem Catalysis; Divergent Synthesis; Palladium; Vinylogous Addition; pi-Lewis Base Catalysis
资金
- NSFC [20931006, 92156005, 21921002]
- China Postdoctoral Science Foundation [2019M663488]
- Postdoctoral Foundation of Sichuan University [2020SCU12019]
This study presents the development of a new asymmetric auto-tandem catalysis process, which allows for the synthesis of diverse compounds with excellent stereocontrol. The use of chiral ligands enables the switchable diastereodivergent synthesis, demonstrating the versatility of this auto-tandem catalysis.
Developing new asymmetric auto-tandem catalysis processes, especially in a divergent manner, is highly attractive but extremely challenging. Presented herein is a palladium-catalyzed auto-tandem reaction between 2,4-dienyl carbonates and o-TsNH arylimines or trifluoroacetophenones that proceeds through a consecutive N-allylation, vinylogous addition, pi-sigma-pi isomerization, and another N-allylation sequence. Importantly, switchable diastereodivergent synthesis could be achieved by tuning the chiral bisphosphine ligands, which led to the construction of a broad spectrum of fused tetrahydroquinoline architectures with moderate to excellent enantioselectivity. Ligand control even enabled effective access to regiodivergent azetidine or chemodivergent beta-H elimination with fair enantioselectivity, further showing the versatility of the current auto-tandem catalysis.
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