185396-37-6Relevant academic research and scientific papers
Construction of chiral α-amino quaternary stereogenic centers via phase-transfer catalyzed enantioselective α-alkylation of α-amidomalonates
Ha, Min Woo,Lee, Myungmo,Choi, Sujee,Kim, Seek,Hong, Suckchang,Park, Yohan,Kim, Mi-Hyun,Kim, Taek-Soo,Lee, Jihoon,Lee, Jae Kyun,Park, Hyeung-Geun
, p. 3270 - 3279 (2015)
An efficient enantioselective synthetic method for α-amido-α-alkylmalonates via phase-transfer catalytic α-alkylation was successfully developed. The α-alkylation of α-amidomalonates under phase-transfer catalytic conditions (50% KOH, toluene, 40 °C) in the presence of (S,S)-3,4,5-trifluorophenyl-NAS bromide afforded the corresponding α-amido-α-alkylmalonates in high chemical yields (up to 99%) and optical yields (up to 97% ee), which could be readily converted to versatile chiral intermediates bearing α-amino quaternary stereogenic centers. The synthetic potential of this methodology was demonstrated via the synthesis of chiral azlactone, oxazoline, and unnatural α-amino acid.
Non-enzymatic diastereoselective asymmetric desymmetrization of 2-benzylserinols giving optically active 4-benzyl-4-hydroxymethyl-2- oxazolidinones: Asymmetric syntheses of α-(hydroxymethyl)phenylalanine, N-Boc-α-methylphenylalanine, cericlamine and BIRT-377
Sugiyama, Shigeo,Arai, Satoshi,Ishii, Keitaro
, p. 8033 - 8045 (2012/10/07)
A reaction of (S)-2-benzyl-2-(α-methylbenzyl)amino-1,3-propanediol (S)-4a and 2-chloroethyl chloroformate, and the subsequent addition of DBU gave (4R,αS)-4-benzyl-4-hydroxymethyl-3-(α-methylbenzyl)-2-oxazolidinone (4R)-5a (92% de) via a diastereoselective asymmetric desymmetrization process. Debenzylation of (4R)-5a using trifluoromethanesulfonic acid and anisole in MeNO2 gave (R)-4-benzyl-4-hydroxymethyl-2-oxazolidinone (R)-15a, which was converted into (R)-(α-hydroxymethyl)phenylalanine (7) in two steps. N-Boc-α-methylphenylalanine (8), cericlami0ne (9) and BIRT-377 (10) were also synthesized using these asymmetric desymmetrization and debenzylation.
Highly enantioselective synthesis of (R)-α-alkylserines via phase-transfer catalytic alkylation of o-biphenyl-2-oxazoline-4-carboxylic acid tert-butyl ester using cinchona-derived catalysts
Lee, Yeon-Ju,Lee, Jihye,Kim, Mi-Jeong,Kim, Taek-Soo,Park, Hyeung-Geun,Jew, Sang-Sup
, p. 1557 - 1560 (2007/10/03)
(Chemical Equation Presented) A highly enantioselective synthetic method for (R)-α-alkylserines was developed by the phase-transfer catalytic alkylation of obiphenyl-2-oxazoline-4-carboxylic acid tert-butyl ester (4i) using cinchona-derived phase-transfer
Asymmetric Syntheses of Both Enantiomers of α-Benzylserine and α-Carboxymethylserine
Horikawa, Manabu,Nakajima, Terumi,Ohfune, Yasufumi
, p. 253 - 254 (2007/10/03)
Both enantiomers of α-benzyl and α-carboxymethyl serines (1, 2) were efficiently synthesized starting with the known phenyl acetol via an intramolecular asymmetric Strecker synthesis.
α-Hydroxymethylphenylglycine and α-hydroxymethylphenylalanine: Synthesis, resolution, and absolute configuration
Olma
, p. 1442 - 1447 (2007/10/03)
Racemic α-hydroxymethylphenylglycine and α-hydroxymethylphenylalanine have been synthesized by selective hydroxymethylation of oxazolones derived from phenylglycine and phenylalanine, and resolved into enantiomers by fractional crystallization of their di
