44812-81-9Relevant academic research and scientific papers
Solid-phase synthesis of peptide selenoesters: Via a side-chain anchoring strategy
Hanna, Cameron C.,Kulkarni, Sameer S.,Watson, Emma E.,Premdjee, Bhavesh,Payne, Richard J.
supporting information, p. 5424 - 5427 (2017/07/06)
Peptide selenoesters have recently emerged as key building blocks for the ligation-based assembly of large polypeptides and proteins. Herein, we report an efficient solid-phase method for the high yielding and epimerisation-free synthesis of peptide selenoesters using a side-chain immobilisation strategy.
Solid-phase synthesis of piperazinones via disrupted ugi condensation
Treder, Adam P.,Tremblay, Marie-Claude,Yudin, Andrei K.,Marsault, Eric
supporting information, p. 4674 - 4677 (2015/03/30)
The first application of aziridine aldehyde dimers in solid-phase synthesis is reported. The solid-supported disrupted Ugi condensation between an aziridine aldehyde dimer, isonitrile, and backbone-anchored amino acids delivered N-acyl aziridine intermediates, which were reacted with nucleophiles to yield the corresponding piperazinones. Subsequent cleavage from the resin provided a diverse set of 2,3,6-trisubstituted piperazinones starting from various amino acids, aziridine aldehydes, and nucleophiles.
The palladium-catalyzed asymmetric α-allylations of carbonyl compounds with chiral allyl esters via enamines and imines
Hiroi,Abe,Suya,Sato,Koyama
, p. 203 - 213 (2007/10/02)
A novel and excellent method for asymmetric α-allylation of carbonyl compounds via their chiral enamines or imines bearing allyl esters has been developed. Readily available chiral allyl esters having chirality at the α- position of the ester carbonyl group, such as (S)-proline and other (S)-α- amino acid allyl esters, have been found to serve as good asymmetric allylating reagents in palladium-catalyzed reactions of the chiral enamines and imines derived from them. The use of (S)-proline or (S)-valine allyl esters as the amino parts in the enamines or imines provided the highest optical yields of the corresponding α-allyl carbonyl compounds. A mechanism for asymmetric induction is proposed based on the stereochemical results obtained.
SYNTHESIS OF α-ALLYL-α-AMINO ACIDS BY MEANS OF A PALLADIUM CATALYIZED INTRAMOLECULAR REARRANGEMENT
Werf, Anne van der,Kellogg, Richard M.
, p. 4981 - 4984 (2007/10/02)
Allylic esters of imines of amino acids provide α-alkylated-α-amino acids in good yields, on rearrangement by catalytic quantities of Pd(0) complexes.
