期刊
ACS CATALYSIS
卷 10, 期 10, 页码 5840-5845出版社
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.0c01293
关键词
nitrosoarenes; cyclopentadienes; gold; enantioselections; nitroso-Povarov
资金
- Ministry of Education [MOE 106N506CE1]
- Ministry of Science and Technology, Taiwan [MOST 1073017-F-007-002]
This work reports gold-catalyzed highly enantioselective nitroso-Povarov reactions between cyclopentadienes and nitrosoarenes in cold dichloroethane, in which nitrosoarenes serve as 4 pi-electron donors and cyclopentadienes as 2 pi-donors. High enantioselectivity has been achieved for substrates over a wide scope. With the same chiral catalyst, nitroso-4-fluorobenzenes in these reactions under DCM/THF/water/air led to oxidative nitroso-Povarov reactions also with high enantioselectivity. We performed O-18-labeling experiments to confirm that both water and O-2 participate in the reactions; these data support a mechanism involving nitrosoarenes as nucleophiles and gold-pi-dienes as electrophiles.
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