81791-30-2

Upstream product

• 115-22-0 3-Hydroxy-3-methyl-2-butanone 
• 123-11-5 4-methoxy-benzaldehyde 
• 81791-31-3 2-(4-Methoxy-phenyl)-5,5-dimethyl-dihydro-furan-3-one 

Downstream Products

• 81791-31-3 2-(4-Methoxy-phenyl)-5,5-dimethyl-dihydro-furan-3-one 
• 123023-79-0 5-(4-methoxyphenyl)-2,2-dimethyl-3(2H)-furanone 
• 1092652-90-8 (E)-4-triethylsilyloxy-1-(4-methoxyphenyl)-4-methylpent-1-en-3-one 
• 130734-40-6 methyl 1,4,5,6-tetrahydro-2-methyl-4-(4-methoxyphenyl)-6-oxopyridine-3-carboxylate 
• 81791-31-3 5-(4-methoxy-phenyl)-2,2-dimethyl-dihydro-furan-3-one 

Relevant academic research and scientific papers

α′-Hydroxyenones as mechanistic probes and scope-expanding surrogates for α,β-unsaturated aldehydes in N-heterocyclic carbene-catalyzed reactions

N-heterocyclic carbene-catalyzed reactions of α,β-unsaturatedaldehydes and a variety of electrophiles allow the facile preparation o f a diverse array of annulation products including trisubstituted cyclopentenes, γ-lactams, and bicyclic β-lactams. The substrate scope of these reactions, however, is limited by the difficulties of preparing the starting α,β-unsaturated aldehydes. We now report that α′- hydroxyenones, which can be prepared in a single convenient step from aromatic and heteroaromatic aldehydes, can serve as efficient surrogates for enals in the annulation reactions. This protocol allows the facile preparation and use of substrates bearing nitrogen heterocycles. These reagents have also allowed us to demonstrate that, in contrast to other classes of aldehydes, the formation of the Breslow intermediate from enals and N-heterocyclic carbenes is irreversible under the reaction conditions.

Copper-catalyzed enantioselective conjugate addition of dialkylzinc reagents to α′-oxy enones

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

Palladium-catalyzed oxidative cyclizations: Synthesis of dihydropyranones and furanones

A boron-mediated syn- and anti-stereoselective aldol reaction giving rise to various β-hydroxyenones was coupled to a Pd(II)-mediated oxidative cyclization to give 2,3,6-trisubstituted syn- and antidihydropyranones in good yields. The Pd(I

α′-hydroxy Enones as Achiral Templates for Lewis Acid-Catalyzed Enantioselective Diels - Alder Reactions

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

Stereoelectronic Control of Intramolecular Michael Addition Reactions

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