Hydroxy-rhodium(I) catalyzed regioselective Michael addition of cyclic enones

Hydroxy-rhodium(I) catalyzed regioselective Michael addition of cyclic enones

An efficient protocol has been accomplished for the synthesis of cyclic α-enone adducts with 2mol% of Rh(I) catalyst. The key feature of this protocol is Rh-OH pre-catalyst performing the carbon–carbon bond formation α- to enone. Further, this method is extended to base-sensitive highly substituted...

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Bibliographic Details
Published in:Tetrahedron letters Vol. 53; no. 9; pp. 1042 - 1044
Main Authors: Kumaraswamy, Gullapalli, Rambabu, Dasa
Format: Journal Article
Language:English
Published: Elsevier Ltd 29-02-2012
Subjects:
Adducts
Cycloheptenone
Cyclohexenone
Dimerization
Hydroxy-rhodium
Michael reaction
Resultants
Tetrahedrons
Transition metal
Cyclohexenone
Transition metal
Hydroxy-rhodium
Dimerization
Cycloheptenone
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Summary:An efficient protocol has been accomplished for the synthesis of cyclic α-enone adducts with 2mol% of Rh(I) catalyst. The key feature of this protocol is Rh-OH pre-catalyst performing the carbon–carbon bond formation α- to enone. Further, this method is extended to base-sensitive highly substituted enones and respective dimerized enone adducts are obtained in moderate to good yields. Hydroxy-rhodium catalyzed dimerization of various cyclic enones to the corresponding α-enone adducts is developed. The key feature of this method is that the base-sensitive, highly substituted enones also undergo dimerization and the resultant products are obtained in moderate to good yields.
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content type line 23
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2011.12.057