32278-29-8Relevant articles and documents
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.