19248-95-4Relevant articles and documents
Synthesis of tubuphenylalanines via ireland-claisen rearrangement
Becker, Dominic,Kazmaier, Uli
, p. 59 - 65 (2013/03/28)
The Ireland-Claisen rearrangement is the central step in the synthesis of tubuphenylalanine, a key building block of the highly antitumor-active tubulysins. The rearrangement of substituted β-amino acid allyl esters, in combination with subsequent decarboxylation and oxidative cleavage of the double bond, allows the highly stereoselective introduction of substituents into the α-position of the resulting σ-amino acids.
Highly enantioselective synthesis of 3-substituted furanones by palladium-catalyzed kinetic resolution of unsymmetrical allyl acetates
Mao, Bin,Ji, Yining,Fananas-Mastral, Martin,Caroli, Giuseppe,Meetsma, Auke,Feringa, Ben L.
supporting information; experimental part, p. 3168 - 3173 (2012/05/05)
Resolving the issue: A near-perfect Pd-catalyzed kinetic resolution of 1,3-disubstituted unsymmetrical allylic acetates uses silyl enol ethers as nucleophiles to access the important 3-substituted-furanone scaffold (see scheme; DACH=diaminocyclohexyl, dba=dibenzylideneacetone). The reaction proceeds under mild conditions and provides the desired products with excellent chemo-, regio-, and enantioselectivity. Copyright
