1122-24-3Relevant articles and documents
α-Branched Ketone Dienolates: Base-Catalysed Generation and Regio- and Enantioselective Addition Reactions
Urruzuno, I?aki,Mugica, Odei,Zanella, Giovanna,Vera, Silvia,Gómez-Bengoa, Enrique,Oiarbide, Mikel,Palomo, Claudio
supporting information, p. 9701 - 9709 (2019/07/12)
In this study, the unique capacity of bifunctional Br?nsted bases to generate α-branched ketone dienolates and control both site- and stereoselectivity of their addition reactions to representative classes of carbon electrophiles (i.e., vinyl sulfones, nitroolefins, formaldehyde) is documented. We demonstrate that by using selected chiral tertiary amine/squaramide catalysts, the reactions of β,γ-unsaturated cycloalkanones proceed through the dienolate Cα almost exclusively and provide all-carbon quaternary cyclic ketone adducts in good yields with very high enantioselectivities. A minor amount (5 %) of γ-addition is observed when nitroolefins are used as electrophiles. The parent acyclic ketone dienolates proved to be less reactive under these conditions, and thus still constitute a challenging class of substrates. Quantum chemical calculations correctly predict these differences in reactivity and explain the observed site-specificity and enantioselectivity.
Gold-catalyzed synthesis of substituted tetrahydronaphthalenes
Grise, Christiane M.,Barriault, Louis
, p. 5905 - 5908 (2007/10/03)
(Diagram presented) We report a gold-catalyzed benzannulation of 3-hydroxy-1,5-enynes to generate tetrahydronaphthalenes. This mild process proves to be an effective method to synthesize various metasubstituted aromatic rings in good yields.
Ethenylation of silyl enol ether with silylethyne
Yamaguchi, Masahiko,Tsukagoshi, Toru,Arisawa, Mieko
, p. 4074 - 4075 (2007/10/03)
-