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- Title
Enantioselective Synthesis of Atropisomeric Biaryl Phosphorus Compounds by Chiral‐Phosphonium‐Salt‐Enabled Cascade Arene Formation.
- Authors
Zhu, Lixiang; Peng, Heling; Guo, Yan; Che, Jixing; Wu, Jia‐Hong; Su, Zhishan; Wang, Tianli
- Abstract
Axially chiral biaryl monophosphorus molecules, exemplified by atropisomeric 1,1′‐biaryl aminophosphines, are significant motifs in numerous chiral ligands/catalysts. Developing efficient methods for preparing phosphorus compounds with these privileged motifs is an important endeavor in synthetic chemistry. Herein, we develop an effective, modular method by a chiral‐phosphonium‐salt‐catalyzed novel cascade between phosphorus‐containing nitroolefins and α,α‐dicyanoolefins, leading to a great diversity of atropisomeric biaryls bearing phosphorus groups in high yields with excellent stereoselectivities. The reaction features include a Thorpe‐type cycloaddition/oxidative hydroxylation/aromatization cascade pathway with a central‐to‐axial chirality transfer process. Insight gained from our studies is expected to advance general efforts towards the catalytic synthesis of atropisomeric biaryl phosphorus compounds, offering a platform for developing new efficient chiral ligands and catalysts.
- Subjects
PHOSPHORUS compounds; NITROALKENES; AROMATIZATION; CHIRALITY; STEREOSELECTIVE reactions
- Publication
Angewandte Chemie, 2022, Vol 134, Issue 30, p1
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.202202467