80227-73-2Relevant articles and documents
Copper-Catalyzed Enantioselective Conjugate Addition to α,β-Unsaturated Aldehydes with Various Organometallic Reagents
Goncalves-Contal, Sylvie,Gremaud, Ludovic,Palais, La?titia,Babel, Lucille,Alexakis, Alexandre
, p. 3301 - 3308 (2016/09/12)
β-Substituted aldehydes constitute a very important class of compounds found in nature. Synthesis of this motif can be envisioned by C-C bond formation on enals. For this purpose, we report herein the development of enantioselective copper-catalyzed conjugate addition of various organometallic reagents to α,β-unsaturated aldehydes with (R)-H8BINAP, (R)-TolBINAP, and (R)-SEGPHOS as chiral ligands. Three sets of conditions were successfully developed and several enals were used. Reactivity and regio- and enantioselectivities were strongly dependent on reaction conditions and substrates. Good to excellent regio- and enantioselectivities were obtained with zinc reagents R2Zn and aluminum reagents R3Al. However, the asymmetric conjugate addition of Grignard reagents afforded only moderate to good regio- and enantioselectivities.
Rearrangement of allylic and propargylic alcohols catalyzed by the combined use of tetrabutylammonium perrhenate(VII) and p-toluenesulfonic acid
Narasaka,Kusama,Hayashi
, p. 2059 - 2068 (2007/10/02)
Allylic rearrangement and/or dehydration reaction of allylic alcohols proceeds smoothly by the use of catalytic amounts of tetrabutylammonium perrhenate and p-toluenesulfonic acid hydrate. Treatment of propargylic alcohols with the catalysts at room temperature affords the rearranged products, α,β-unsaturated carbonyl compounds, while β,γ-unsaturated ketones are obtained as main products by the reaction in refluxing 1,2-dichloroethane. The application of this catalytic system is also described for the preparation of some synthetic intermediates.
Reactions of 3-Hydroxyvinyl Selenones with Alkoxides. Oxetane Formation and Fragmentation Reactions
Shimizu, Makoto,Ando, Ryoichi,Kuwajima, Isao
, p. 1230 - 1238 (2007/10/02)
3-Hydroxyvinyl phenyl selenones are prepared and their behavior as conjugate addition acceptors has been investigated.As a result, a selenonyl group has been found to activate the C=C bond for conjugate addition of nucleophiles and further to behave as an