Subject(s)
Cyclopentanes/chemistry , Phosphines/chemistry , Carbon/chemistry , Catalysis , Cycloaddition ReactionABSTRACT
A novel domino annulation between sulfur ylides and salicyl N-thiophosphinyl imines was developed. The method allows the synthesis of a highly substituted trans-2,3-dihydrobenzofuran skeleton with high yield and excellent chemo- and stereoselectivity.
ABSTRACT
A novel NHC-catalyzed three-component domino strategy to access high functionalized cis-ε-ketoesters with excellent yields (up to 98%) and high stereoselectivities (up to 20:1) is documented. The title domino reactions are atom economical and work on a broad range of substrates. The relative stereochemistry could be explained by a cascade crossed-benzoin/oxy-Cope rearrangement/esterification process. The thus-obtained products are of potential synthetic value in the drug research and combinatorial chemistry.
ABSTRACT
A novel domino reaction catalyzed by triphenylphosphine was developed for synthesis of the highly functionalized chroman derivatives. The first example that the gamma-CH(3) of allenoate undergoes cyclization to form chroman derivates was reported.