期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 57, 期 27, 页码 8225-8229出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201804614
关键词
asymmetric catalysis; carbocations; organocatalysis; rearrangements; strained molecules
资金
- Spanish MINECO [FEDER-CTQ2017-83633-P, FEDER-CTQ2016-76155-R]
- Basque Government [IT908-16]
- UPV/EHU
- Government of Aragon (Grupos de Referencia) [E34-R17]
Racemic cyclopropyl ketones undergo enantioselective rearrangement to deliver the corresponding dihydrofurans in the presence of a chiral phosphoric acid as the catalyst. The reaction involves activation of the donor-acceptor cyclopropane substrate by the chiral BrOnsted acid catalyst to promote the ring-opening event, thus generating a carbocationic intermediate that subsequently undergoes cyclization. Computational studies and control experiments support this mechanistic pathway.
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