87974-86-5Relevant academic research and scientific papers
Enantiodivergent Synthesis of (+)- and (?)-Pyrrolidine 197B: Synthesis of trans-2,5-Disubstituted Pyrrolidines by Intramolecular Hydroamination
Pérez, Sixto J.,Purino, Martín A.,Cruz, Daniel A.,López-Soria, Juan M.,Carballo, Rubén M.,Ramírez, Miguel A.,Fernández, Israel,Martín, Víctor S.,Padrón, Juan I.
supporting information, p. 15529 - 15535 (2016/10/13)
A highly efficient, diastereoselective, iron(III)-catalyzed intramolecular hydroamination/cyclization reaction involving α-substituted amino alkenes is described. Thus, enantiopure trans-2,5-disubstituted pyrrolidines and trans-5-substituted proline derivatives were synthesized by means of a combination of enantiopure starting materials, easily available from l-α-amino acids, with sustainable metal catalysts such as iron(III) salts. The scope of this methodology is highlighted in an enantiodivergent approach to the synthesis of both (+)- and (?)-pyrrolidine 197B alkaloids from l-glutamic acid. In addition, a computational study was carried out to gain insight into the complete diastereoselectivity of the transformation.
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.
Highly enantioselective hydrogenation of exocyclic double bond of N-tosyloxazolidinones catalyzed by a neutral rhodium complex and its synthetic applications
Shen, Zengming,Lu, Xiyan,Lei, Aiwen
, p. 9237 - 9246 (2007/10/03)
A highly enantioselective synthesis of optically active N-tosyl-4-alkyl-1,3-oxazolidin-2-ones based on the asymmetric hydrogenation of the trisubstituted exocyclic double bond of N-tosyl-4-alkylidene-1,3-oxazolidin-2-ones under the catalysis of neutral [R
LES ORGANOCUPRATES DANS UNE NOUVELLE SYNTHESE D'AMINOACIDES ENANTIOMERIQUEMENT PURS
Bajgrowicz, J. A.,Hallaoui, A. El,Jacquier, R.,Pigiere, Ch.,Viallefont, Ph.
, p. 1833 - 1845 (2007/10/02)
A new general method of synthesis of optically pure α- amino esters was elaborated during studies on the reaction of organocuprates with tosyl and halogeno derivatives of L-serine and L-homoserine.
LITHIUM DIORGANOCUPRATE REACTIONS WITH L-SERINE DERIVATIVES
Bajgrowicz, J. A.,Hallaoui, A. El,Jacquier, R.,Pigiere, Ch.,Viallefont, Ph.
, p. 2759 - 2762 (2007/10/02)
The lithium diorganocuprate reactions with L-serine derivatives are studied.Retention of configuration, or at least a high enantiomeric excess (> 80percent) of the formed α-amino esters is observed in all cases.Attempts are made to restrict side-reactions.
