85736-13-6Relevant articles and documents
α′-hydroxy Enones as Achiral Templates for Lewis Acid-Catalyzed Enantioselective Diels - Alder Reactions
Palomo, Claudio,Oiarbide, Mikel,Garcia, Jesus M.,Gonzalez, Alberto,Arceo, Elena
, p. 13942 - 13943 (2003)
α′-Hydroxy enones react with dienes in the presence of (S,S)-[Cu(tBu-box)](OTf)2 or (S,S)-[Cu(tBu-box)](SbF6)2 (2 to 10 mol %) to afford the corresponding Diels?Alder adducts in high yield and selectivity. Isomeric ratios (regioselectivity, endo/exo or cis/trans) of up to >99:1 and ee values of up to >99% are obtained. Significantly, difficult dienes such as isoprene, 2,3-dimethyl butadiene and piperylene behave satisfactorily. Subsequent oxidative cleavage of the ketol in the resulting cycloadducts by treatment with cerium ammonium nitrate (CAN) yields the corresponding enantiopure carboxylic acids. Alternatively, carbonyl addition and subsequent diol cleavage with CAN produces the corresponding ketone adducts. Copyright
Copper-catalyzed enantioselective conjugate addition of dialkylzinc reagents to α′-oxy enones
Garcia, Jesus M.,Gonzalez, Alberto,Kardak, Bharat G.,Odriozola, Jose M.,Oiarbide, Mikel,Razkin, Jesus,Palomo, Claudio
supporting information; experimental part, p. 8768 - 8771 (2009/10/01)
The copper-catalyzed enantioselective conjugate addition of dialkylzinc reagents to α'-oxy enones was investigated. Cu(OTf)2, ligand, and toluene were placed in a flame-dried Schlenk tube. the resulting mixture was stirred at room temperature f
Stereoelectronic Control of Intramolecular Michael Addition Reactions
Ellis, Graham W. L.,Johnson, C. David,Rogers, David N.
, p. 5090 - 5095 (2007/10/02)
Concepts of stereoelectronic control lead to the conclusion that the 5-endo-trig ring closure of (E)-2-methyl-3-oxo-5-phenylpent-4-en-2-ol should be disfavored.However, the acid-catalyzed ring closure in trifluoroacetic acid occurs readily, suggesting an