169221-12-9Relevant academic research and scientific papers
Silylation-based kinetic resolution of α-hydroxy lactones and lactams
Clark, Robert W.,Deaton, T. Maxwell,Zhang, Yan,Moore, Maggie I.,Wiskur, Sheryl L.
supporting information, p. 6132 - 6135 (2014/01/17)
A silylation-based kinetic resolution has been developed for α-hydroxy lactones and lactams employing the chiral isothiourea catalyst (-)-benzotetramisole and triphenylsilyl chloride as the silyl source. The system is more selective for lactones than lactams, and selectivity factors up to 100 can be achieved utilizing commercially available reagents.
A synthesis of levetiracetam based on (S)-N-phenylpantolactam as a chiral auxiliary
Boschi, Francesca,Camps, Pelayo,Comes-Franchini, Mauro,Munoz-Torrero, Diego,Ricci, Alfredo,Sanchez, Laura
, p. 3739 - 3745 (2007/10/03)
The synthesis of levetiracetam and its enantiomer by deracemization of (±)-2-bromobutyric acid using either (S)- or (R)-N-phenylpantolactam as chiral auxiliaries, followed by SN2 substitution of the bromine atom by a 2-oxopyrrolidin-1-yl group and amidation of the carboxylic acid, is described.
Synthesis of both enantiomers of baclofen using (R)- and (S)-N-phenylpantolactam as chiral auxiliaries
Camps, Pelayo,Munoz-Torrero, Diego,Sanchez, Laura
, p. 2039 - 2044 (2007/10/03)
Esterification of racemic 4-nitro-3-(4-chlorophenyl)butanoic acid with (R)- or (S)-N-phenylpantolactam as the chiral auxiliary allowed us to obtain the (3R,3′R)- or (3S,3′S)-nitro esters with >98:2 dr after column chromatography. Hydrolysis of the resulti
Stereoselective synthesis of both enantiomers of N-Boc-α-aryl- γ-aminobutyric acids
Camps, Pelayo,Munoz-Torrero, Diego,Sanchez, Laura
, p. 311 - 321 (2007/10/03)
Esterification of racemic α-aryl-β-cyanopropionic acid chlorides with either (R)- or (S)-N-phenylpantolactam as the chiral auxiliary in the presence of Et3N resulted in the predominant formation of (αR,3′R)- or (αS,3′S)-configured pantolactam c
Enantioselective synthesis of both enantiomers of 3-hydroxy-4,4-dimethyl-1-phenyl-2-pyrrolidinone
Camps, Pelayo,Perez, Francesc,Soldevilla, Nuria
, p. 6853 - 6856 (2007/10/03)
The chiral auxiliaries (R)- and (S)-3-Hydroxy-4,4-dimethyl-1-phenyl-2-pyrrolidinone were obtained in good yield and e.e. by enantioselective reduction of 4,4-dimethyl-1-phenylpyrrolidine-2,3-dione with (-)- and (+)-B-chlorodiisopinocamphenylborane, (-)- and (+)-DIP-Chloride, respectively. The (R)-enantiomer was also obtained by enantioselective hydrogenation of the same precursor using a complex of 1,5-cyclooctadiene Rh(I) and (2S,4S)-1-(tert-butoxycarbonyl)-4-(diphenylphosphino)-2-(diphenylphosphinomethyl )pyrrolidine, (S,S)-BPPM, as the chiral catalyst.
(R)- and (S)-3-hydroxy-4,4-dimethyl-1-phenyl-2-pyrrolidinone by lipase-catalyzed resolution of the racemic mixture: New chiral auxiliaries related to pantolactone
Camps,Gimenez,Font-Bardia,Solans
, p. 985 - 990 (2007/10/03)
(R)- and (S)-3-hydroxy-4,4-dimethyl-1-phenyl-2-pyrrolidinone (R)- and (S)-1 have been prepared by lipase-catalyzed enantioselective acetylation of (S)-1 from rac-1 with vinyl acetate. Controlled hydrolysis of the acetate (S)-2 gave (S)-1. The configuration of (R)-1 and its p-bromobenzoate (R)-3 were established by X-ray diffraction analysis.
