7146-63-6Relevant academic research and scientific papers
Halofluorination of N-protected α,β-dehydro-α-amino acid esters—A convenient synthesis of α-fluoro-α-amino acid derivatives
Ulbrich, Dirk,Daniliuc, Constantin G.,Haufe, Günter
supporting information, p. 65 - 75 (2016/07/11)
N-protected dehydroamino acid methyl esters have been converted to α-fluoro-β-halo amino acid derivatives under halofluorination reaction conditions. The influences of the nitrogen protecting group of the substrates and of the halonium electrophile on the reaction outcome and the stability of the obtained products have been studied. Furthermore, reduction of the halogen substituent (Cl or Br) under radical conditions provided a possibility for follow-up reactions. Nucleophilic substitution reactions, however, failed.
Stereoselective synthesis of chiral α-amino-β-lactams through palladium(II)-catalyzed sequential monoarylation/amidation of C(sp 3)-H Bonds
Zhang, Qi,Chen, Kai,Rao, Weihao,Zhang, Yuejun,Chen, Fa-Jie,Shi, Bing-Feng
supporting information, p. 13588 - 13592 (2014/01/06)
Give Me an Ar, give Me an N! Arylation of the methyl group in a simple derivative of readily available alanine under palladium catalysis was followed by intramolecular amidation at the same position to give chiral α-amino-β-lactams with a wide range of aryl substituents (see scheme; Phth=phthaloyl). The α-amino-β-lactams were obtained in moderate to high yields with good functional-group tolerance and high diastereoselectivity. Copyright
Efficient Access to Alanine Derivatives by 1,4-Additions of Potassium Trifluoro(organo)borates
Navarre, Laure,Darses, Sylvain,Genet, Jean-Pierre
, p. 69 - 73 (2007/10/03)
Potassium trifluoro(organo)borates, highly stable and easily prepared organoboran derivatives, were able to react with a great variety of dehydroamino esters. This reaction, catalyzed by rhodium complexes, allowed the formation of alanine derivatives bearing a great variety of amino protecting groups in good to high yields.
A mild, selective, PyBOP mediated procedure for the conversion of primary Amines into phthalimides
Aguilar, Núria,Moyano, Albert,Pericàs, Miquel A.,Riera, Antoni
, p. 313 - 316 (2007/10/03)
A new method for the protection of primary amines or amino alcohols as phthalimides is described. The phthaloyl group is selectively introduced under mild, anhydrous conditions by reacting the amine with 2- (ethoxycarbonyl)benzoic acid activated by PyBOP, followed by the thermally induced cyclization of the resulting phthalamic ester. These reaction conditions are applicable to a variety of primary amines and good yields are obtained in all cases.
CESIUM FLUORIDE-PROMOTED SYNTHESIS OF CARBOXYLIC ACID DERIVATIVES USING 2-FLUOROPYRIDINIUM SALT
Shoda, Shin-ichiro,Mukaiyama, Teruaki
, p. 391 - 392 (2007/10/02)
In the presence of cesium fluoride, the equimolecular reactions of carboxylic acids with alcohols, amines or thiols using 2-fluoro-pyridinium salt proceeded smoothly under mild conditions to afford the corresponding carboxylic acid derivatives with base s
