727381-76-2Relevant academic research and scientific papers
Highly effective vinylogous Mukaiyama-Michael reaction catalyzed by silyl methide species generated from 1,1,3,3-tetrakis(trifluoromethanesulfonyl)propane
Takahashi, Arata,Yanai, Hikaru,Zhang, Min,Sonoda, Takaaki,Mishima, Masaaki,Taguchi, Takeo
supporting information; experimental part, p. 1259 - 1265 (2010/04/29)
(Chemical Equation Presented) Silyl methide species in situ generated from 1,1,3,3-tetrakis(trifluoromethanesulfonyl)propane (Tf2CHCH 2CHTf2) performed as an excellent acid catalyst for the vinylogousMukaiyama-Michael reaction of α,β-unsaturated ketones with 2-silyloxyfurans. Notably, the required loading of Tf2CHCH 2CHTf2 to obtain the 1,4-adducts in reasonable yield was significantly low (from 0.05 to 1.0 mol%). This carbon acid-mediatedVMMreaction provides a powerful synthetic methodology to construct highly substituted γ-butenolide structure. 2010 American Chemical Society.
Sml2-promoted reformatsky-type coupling reactions in exceptionally hindered contexts
Sparling, Brian A.,Moslin, Ryan M.,Jamison, Timothy F.
supporting information; experimental part, p. 1291 - 1294 (2009/04/08)
Highly substituted, very hindered enones were synthesized using a two-step procedure that utilizes a diiodosamarium-promoted Reformatsky-type coupling and dehydration using Martin sulfurane. Both α-chloro- and α-bromoketones were coupled with a variety of carbonyl nucleophiles to form the intermediate β-hydroxyketones, occurring with excellent diastereoselectivity, favoring the syn isomer (R1 = Me). This technique complements other methods and enables the preparation of enones outside of the scope of current olefination methodology.
