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1.
Chemistry ; 16(32): 9890-904, 2010 Aug 23.
Article in English | MEDLINE | ID: mdl-20540048

ABSTRACT

The copper-catalyzed conjugate addition of Grignard reagents to 3-substituted cyclic enones allows the formation of all-carbon chiral quaternary centers. We demonstrate in this article that N-heterocyclic carbenes act as efficient chiral ligands for this transformation. High enantioselectivities (up to 96% ee) could be obtained for a variety of substrates.

3.
J Am Chem Soc ; 128(26): 8416-7, 2006 Jul 05.
Article in English | MEDLINE | ID: mdl-16802804

ABSTRACT

The copper-catalyzed asymmetric conjugate addition of Grignard reagents to trisubstituted cyclic enones affords enantioenriched all-carbon quaternary centers with up to 96% ee. The chiral ligand is a diaminocarbene, directly generated in situ. The combination of Grignard reagent and diaminocarbene is unprecedented in conjugate addition, and the additon of the phenyl group, on such enones, cannot be done by other conjugate addition methods.


Subject(s)
Copper/chemistry , Ketones/chemistry , Organometallic Compounds/chemistry , Catalysis , Free Radicals/chemical synthesis , Free Radicals/chemistry , Indicators and Reagents/chemistry , Ligands , Molecular Structure , Stereoisomerism
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