期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 57, 期 19, 页码 5454-5458出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201802316
关键词
asymmetric catalysis; cycloadditions; photoredox catalysis; cyclopentenes; cyclopropanes
资金
- Deutsche Forschungsgemeinschaft [ME 1805/13-1]
The herein reported visible-light-activated catalytic asymmetric [3+2] photocycloadditions between cyclopropanes and alkenes or alkynes provide access to chiral cyclopentanes and cyclopentenes, respectively, in 63-99% yields and with excellent enantioselectivities of up to >99% ee. The reactions are catalyzed by a single bis-cyclometalated chiral-at-metal rhodium complex (2-8mol%) which after coordination to the cyclopropane generates the visible-light-absorbing complex, lowers the reduction potential of the cyclopropane, and provides the asymmetric induction and overall stereocontrol. Enabled by a mild single-electron-transfer reduction of directly photoexcited catalyst/substrate complexes, the presented transformations expand the scope of catalytic asymmetric photocycloadditions to simple mono-acceptor-substituted cyclopropanes affording previously inaccessible chiral cyclopentane and cyclopentene derivatives.
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