43188-65-4Relevant academic research and scientific papers
Asymmetric Synthesis of β2-Aryl Amino Acids through Pd-Catalyzed Enantiospecific and Regioselective Ring-Opening Suzuki–Miyaura Arylation of Aziridine-2-carboxylates
Takeda, Youhei,Matsuno, Tetsuya,Sharma, Akhilesh K.,Sameera,Minakata, Satoshi
, p. 10226 - 10231 (2019)
A Pd-catalyzed enantiospecific and regioselective ring-opening Suzuki–Miyaura arylation of aziridine-2-carboxylates was developed. The cross-coupling allows for the asymmetric preparation of enantioenriched β2-aryl amino acids, starting from co
Studies on the synthesis of orthogonally protected azalanthionines, and of routes towards β-methyl azalanthionines, by ring opening of N-activated aziridine-2-carboxylates
O'Brien, Keith,ó Proinsias, Keith,Kelleher, Fintan
supporting information, p. 5082 - 5092 (2014/07/08)
Orthogonally protected azalanthionines were successfully synthesised by the ring-opening of N-activated aziridine-2-carboxylates with protected diaminopropanoic acids (DAPs). The required DAPs were also prepared by ring-opening of N-activated aziridine-2-carboxylates with para- methoxybenzylamine, but it was found that the choice of aziridine protecting groups dictated both the success of the reaction as well as the regioselectivity of the isolated products. Attempts to extend the methodology to the preparation of the more sterically demanding β-methyl azalanthionines have, so far, been unsuccessful.
New methodology for the preparation of N-tosyl aziridine-2-carboxylates
Marzorati, Liliana,Barazzone, Giovana C.,Bueno Filho, Marco A.,Wladislaw, Blanka,Di Vitta, Claudio
, p. 6509 - 6513 (2008/02/13)
N-Tosyl aziridine-2-carboxylate methyl esters were prepared from methyl N-tosyl-l-serinate or N-tosyl-l-threoninate, tosyl chloride, and K2CO3, under phase-transfer catalysis (PTC) conditions. The same methodology, as applied to the
Synthesis of α-amino acids by reaction of aziridine-2-carboxylic acids with carbon nucleophiles
Beresford, Kenneth J. M.,Church, Nicola J.,Young, Douglas W.
, p. 2888 - 2897 (2008/02/08)
A variety of homochiral α-amino acids have been prepared in good yield via regioselective reaction of higher order cuprates with (2S)-N-para-toluenesulfonylaziridine-2-carboxylic acid 4. The reaction was much less regioselective and low yielding when higher order cuprates were reacted with the more hindered aziridine carboxylic acid 30, the principal products being protected β-amino acids. Reaction of lithium trimethylsilylacetylide with the aziridine acid 30, however, gave a protected α-amino acid which was converted to the protected isoleucine ester 37. The Royal Society of Chemistry 2006.
Reduction of 2-acylaziridines by samarium(II) iodide. An efficient and regioselective route to β-amino carbonyl compounds
Molander, Gary A.,Stengel, Peter J.
, p. 8887 - 8912 (2007/10/03)
A convenient method for the reduction of 2-acylaziridines, aziridine-2- carboxylates and aziridine-2-carboxamides is described. The reduction of all of the substrates examined was extremely rapid and highly regioselective, giving rise to β-amino carbonyl compounds. This method appears to be general for all of the classes of aziridines mentioned above, and also tolerates a variety of nitrogen protecting groups.
Synthesis of functionalized cyclopropanes by MIRC reactions of aziridinyl-methylenemalonates
Funaki, Ikuo,Bell, Roel P.L.,Thijs, Lambertus,Zwanenburg, Binne
, p. 12253 - 12274 (2007/10/03)
The synthesis of cyclopropane derivatives via a MIRC reaction of aziridinyl-methylene-malonates is described. In this way it is possible to introduce a hydrogen, a phenylthio, a tributylstannyl and an olefinic function at the cyclopropane ring, that further contains an alkylamino substituent. Addition of CuCN catalyzed Grignard reagents gave the most promising results. The diastereoselectivity was dependent on the aziridine nitrogen substituent and the bulkiness of the reagent.
Synthesis of α-Amino Acids by Ring Opening of Aziridine-2-carboxylates with Carbon Nucleophiles
Church, Nicola J.,Young, Douglas W.
, p. 151 - 154 (2007/10/02)
Excellent regiospecificity has been achieved in the reaction of carbon nucleophiles with N-para-toluenesulfonylaziridine-2-carboxylic acid (6, R=H) protected as the anion.This has been developed into a general and high yielding synthesis of optically pure α-amino acids containing one chiral centre.When the aziridine (20) containing a second chiral centre was used, only lithium trimethylsilylacetylide gave the desired α-amino acid.Reaction with higher order cuprates gave lower yields, the principal products being the protected β-amino acids (22) and (23).
SRUCTURE AND SYNTHESIS OF FR900490, A NEW IMMUNOMODULATING PEPTIDE ISOLATED FROM A FUNGUS
Shigematsu, Nobuharu,Setoi, Hiroyuki,Uchida, Itsuo,Shibata, Toshihiro,Terano, Hiroshi,Hashimoto, Masashi
, p. 5147 - 5150 (2007/10/02)
The structure of FR900490 (C14H22N6O6) has been shown to be 1 on the basis of its physical and chemical properties and confirmed by a synthesis.
