Rhodium( iii )-catalyzed asymmetric [4+1] spiroannulations of O -pivaloyl oximes with α-diazo compounds

Chiral Rh III catalysts can catalyze the asymmetric [4+1] spiroannulation of O -pivaloyl oximes with α-diazo homophthalimides under redox-neutral and acid/base-neutral conditions, leading to formation of chiral spirocyclic imines as a result of C–H activation and N–O cleavage. The reaction proceeded...

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Published inChemical communications (Cambridge, England) Vol. 57; no. 67; pp. 8268 - 8271
Main Authors Sun, Lincong, Liu, Bingxian, Zhao, Yanlian, Chang, Junbiao, Kong, Lingheng, Wang, Fen, Deng, Wei-Qiao, Li, Xingwei
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 28.08.2021
Royal Society of Chemistry
Subjects
Asymmetry
carbon-hydrogen bond activation
Chemistry
Chemistry, Multidisciplinary
Crystallography
Imines
Oximes
Physical Sciences
Rhodium
Science & Technology
Substrates
3+2 ANNULATION
CATALYSIS
ACTIVATION
HYDROGENATION
LIGANDS
1,3-DIENES
BIARYL COMPOUNDS
C(SP)-H
C-H FUNCTIONALIZATION
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ISSN1359-7345
1364-548X
1364-548X
DOI10.1039/D1CC02888J

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Summary:Chiral Rh III catalysts can catalyze the asymmetric [4+1] spiroannulation of O -pivaloyl oximes with α-diazo homophthalimides under redox-neutral and acid/base-neutral conditions, leading to formation of chiral spirocyclic imines as a result of C–H activation and N–O cleavage. The reaction proceeded with high efficiency and features broad substrate scope, mild reaction conditions, and high to excellent enantioselectivities.
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ISSN:1359-7345
1364-548X
1364-548X
DOI:10.1039/D1CC02888J