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Title
| - Palladium(0)-Catalyzed Regioselective Synthesis ofα-Dehydro-β-amino Esters from Amines and Allyl Acetates: Synthesis of a α-Dehydro-β-amino Acid Derived Cyclic Peptide asa Constrained β-Turn Mimic
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Abstract
| - Acetates derived from the adducts of the Baylis−Hillman reaction can be reacted in a regioselectivemanner with amines in the presence of palladium(0) catalyst to afford α-dehydro-β-amino esters(2 and 3) in good yields. The regioselectivity of the reaction can be controlled by temperature andreaction medium leading to the synthesis of regioisomers 2 or 3. The α-dehydro-β-amino acid 3 isa turn inducer, and the dipeptides 6 derived from it show the presence of an eight-memberedintramolecular hydrogen bond. Also, cobalt(II) chloride catalyzes the cleavage of epoxy peptideswith α-dehydro-β-amino acid derivative 3b to afford the corresponding dipeptide derivatives 8,which exhibit an intramolecular hydrogen bond and thus mimic a β-turn. This intramolecularhydrogen bonding preorganizes the corresponding diallylated peptide 8c for cyclization via ring-closing metathesis to afford the cyclic peptide 9 as a constrained mimic of a β-turn.
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