Catalytic asymmetric synthesis of diphenylbutazone analogues

The asymmetric Michael addition of diphenylbutazone and its analogues to α,β-unsaturated 2-acyl imidazoles has been developed with a chiral-at-metal Rh( iii ) complex as a catalyst. The corresponding adducts were obtained in good yields (89-98%) with excellent enantioselectivities (up to >99%). T...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2018-09, Vol.54 (74), p.1479-1482
Main Authors: Li, Shi-Wu, Kang, Qiang
Format: Article
Language:English
Subjects:
Adducts
Catalysis
Catalysts
Chemical synthesis
Coordination compounds
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Summary:The asymmetric Michael addition of diphenylbutazone and its analogues to α,β-unsaturated 2-acyl imidazoles has been developed with a chiral-at-metal Rh( iii ) complex as a catalyst. The corresponding adducts were obtained in good yields (89-98%) with excellent enantioselectivities (up to >99%). The reaction can be conducted on a gram-scale with a low catalyst loading (0.04 mol%) without impacting its efficiency. Moreover, the adducts can be converted into other useful synthetic building blocks. The asymmetric Michael addition of diphenylbutazone and its analogues to α,β-unsaturated 2-acyl imidazoles has been developed with a chiral-at-metal Rh( iii ) complex as a catalyst.
ISSN:1359-7345
1364-548X
DOI:10.1039/c8cc06426a