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- W2952192015 abstract "Acetates derived from the adducts of the Baylis-Hillman reaction can be reacted in a regioselective manner with amines in the presence of palladium(0) catalyst to afford alpha-dehydro-beta-amino esters (2 and 3) in good yields. The regioselectivity of the reaction can be controlled by temperature and reaction medium leading to the synthesis of regioisomers 2 or 3. The alpha-dehydro-beta-amino acid 3 is a turn inducer, and the dipeptides 6 derived from it show the presence of an eight-membered intramolecular hydrogen bond. Also, cobalt(II) chloride catalyzes the cleavage of epoxy peptides with alpha-dehydro-beta-amino acid derivative 3b to afford the corresponding dipeptide derivatives 8, which exhibit an intramolecular hydrogen bond and thus mimic a beta-turn. This intramolecular hydrogen 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 beta-turn." @default.
- W2952192015 created "2019-06-27" @default.
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- W2952192015 creator A5035750560 @default.
- W2952192015 creator A5038250843 @default.
- W2952192015 date "2002-10-03" @default.
- W2952192015 modified "2023-10-03" @default.
- W2952192015 title "Palladium(0)-Catalyzed Regioselective Synthesis of α-Dehydro-β-amino Esters from Amines and Allyl Acetates: Synthesis of a α-Dehydro-β-amino Acid Derived Cyclic Peptide as a Constrained β-Turn Mimic" @default.
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- W2952192015 doi "https://doi.org/10.1021/jo010981d" @default.
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