Journal
CHEMICAL SCIENCE
Volume 7, Issue 2, Pages 1474-1479Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c5sc04138d
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Funding
- NIH [GM069559]
- NATIONAL INSTITUTE OF GENERAL MEDICAL SCIENCES [R01GM069559] Funding Source: NIH RePORTER
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The Rh(III)-catalyzed cascade addition of a C-H bond across alkene and carbonyl pi-bonds is reported. The reaction proceeds under mild reaction conditions with low catalyst loading. A range of directing groups were shown to be effective as was the functionalization of alkenyl in addition to aromatic C(sp(2))-H bonds. When the enone and aldehyde electrophile were tethered together, cyclic beta-hydroxy ketones with three contiguous stereocenters were obtained with high diastereoselectivity. The intermolecular three-component cascade reaction was demonstrated for both aldehyde and imine electrophiles. Moreover, the first X-ray structure of a cationic Cp*Rh(III) enolate with interatomic distances consistent with an eta(3)-bound enolate is reported.
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