160788-63-6Relevant 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.
Dual Catalytic Decarboxylative Allylations of α-Amino Acids and Their Divergent Mechanisms
Lang, Simon B.,O'Nele, Kathryn M.,Douglas, Justin T.,Tunge, Jon A.
supporting information, p. 18589 - 18593 (2016/01/25)
The room temperature radical decarboxylative allylation of N-protected α-amino acids and esters has been accomplished via a combination of palladium and photoredox catalysis to provide homoallylic amines. Mechanistic investigations revealed that the stability of the α-amino radical, which is formed by decarboxylation, dictates the predominant reaction pathway between competing mechanisms.
Safe Removal of the Allyl Protecting Groups of Allyl Esters using a Recyclable, Low-Leaching and Ligand-Free Palladium Nanoparticle Catalyst
Takagi, Koji,Fukuda, Hayato,Shuto, Satoshi,Otaka, Akira,Arisawa, Mitsuhiro
supporting information, p. 2119 - 2124 (2015/06/23)
A safe, facile and low-leaching (up to 0.04ppm) method has been developed for the removal of allyl, prenyl and benzyl protecting groups from the corresponding esters, using a sulfur-modified gold-supported palladium (SAPd) nanoparticle catalyst, which is known to be non-flammable. The catalyst itself was found to be recyclable and the reaction appeared to proceed on the surface of the SAPd.
Decarboxylative allylation of amino alkanoic acids and esters via dual catalysis
Lang, Simon B.,O'Nele, Kathryn M.,Tunge, Jon A.
supporting information, p. 13606 - 13609 (2015/02/02)
A combination of photoredox and palladium catalysis has been employed to facilitate the room temperature decarboxylative allylation of recalcitrant amino and phenylacetic allyl esters. This operationally simple process produces CO2as the only b
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.
Selective esterifications of primary alcohols in a water-containing solvent
Wang, Yong,Aleiwi, Bilal A.,Wang, Qinghui,Kurosu, Michio
supporting information, p. 4910 - 4913,4 (2012/12/12)
Oxyma and an oxyma derivative, (2,2-dimethyl-1,3-dioxolan-4-yl)methyl 2-cyano-2-(hydroxyimino)acetate (5b), displayed a remarkable effect on selective esterifications of primary alcohols. A wide range of carboxylic acids could be esterified with primary alcohols by using EDCI, NaHCO3, and Oxyma or Oxyma derivative 5b in 5% H2O-CH3CN. Oxyma derivative 5b is particularly useful, since it could be removed after the reaction via a simple basic or an acidic aqueous workup procedure.
Selective esterifications of primary alcohols in a water-containing solvent
Wang, Yong,Aleiwi, Bilal A.,Wang, Qinghui,Kurosu, Michio
supporting information, p. 4910 - 4913 (2013/01/15)
Oxyma and an oxyma derivative, (2,2-dimethyl-1,3-dioxolan-4-yl)methyl 2-cyano-2-(hydroxyimino)acetate (5b), displayed a remarkable effect on selective esterifications of primary alcohols. A wide range of carboxylic acids could be esterified with primary alcohols by using EDCI, NaHCO3, and Oxyma or Oxyma derivative 5b in 5% H2O-CH3CN. Oxyma derivative 5b is particularly useful, since it could be removed after the reaction via a simple basic or an acidic aqueous workup procedure.
Synthesis of dipeptide isosteres by cross-metathesis
Enholm, J. Eric,Low, Tammy,Cooper, Daniel,Ghivirija, Ion
experimental part, p. 6920 - 6927 (2012/08/29)
This work describes the attachment of two amino acid derivatives by olefin cross-metathesis using Grubbs' second generation catalyst. They were connected at the carboxyl termini. In addition, a cyclic dilactam scaffold was used, which reacted with only a
Using cross-metathesis to couple L-phenylalanine to a macrocyclic lactam
Enholm, Eric,Low, Tammy
, p. 2272 - 2276 (2007/10/03)
Grubbs' second generation ruthenium catalyst was used to couple the amino acid L-phenylalanine to a 17-membered lactam, using cross-metathesis with an E-alkene favored in the process. The best coupling conditions gave the product in 48% yield. The reversi
A novel 1-tert-butoxy-2-tert-butoxycarbonyl-1,2-dihydroisoquinoline (BBDI)-catalyzed esterification of N-protected amino acids with nearly equimolar amounts of alcohols in the presence of Boc2O
Saito, Yukako,Watanabe, Tomokazu,Takahata, Hiroki
, p. 3099 - 3102 (2007/10/03)
A very mild, BBDI-catalyzed esterification using approximately equimolar amounts of N-protected amino acids and alcohols, in junction with Boc2O is described.
