Reaction of Organolead Triacetates with 4-Ethoxycarbonyl-2-methyloxazol-5-one. The Synthesis of α-Aryl and α-Vinyl N-Acetylglycine Ethyl Esters and Their Enzymic Resolution.
An efficient synthesis of the moisture-sensitive compound, 4-ethoxycarbonyl-2-methyloxazol-5-one, has been achieved.This compound undergoes high-yielding arylation and vinylation at the 4-position with organolead triacetates to give compounds which in water are converted to α-aryl and α-vinyl N-acetylglycine ethyl esters.These α-substituted glycine derivatives may be kinetically resolved in very good yield and high enantiomeric excess by enzymic hydrolysis of either the ester group or the amide function of the corresponding carboxylic acids.
Resolution of N-protected amino acid esters using whole cells of Candida parapsilosis ATCC 7330
Whole cells of Candida parapsilosis ATCC 7330 were used for the resolution of N-acetyl amino acid esters. Excellent enantioselectivities (E = 40 to >500) were achieved for the resolution of N-protected protein and non-protein amino acid esters giving good yields (28-50%) and high enantiomeric excesses (up to >99%) for both enantiomers.
Stella, Selvaraj,Chadha, Anju
experimental part
p. 457 - 460
(2010/06/21)
Diastereoselective synthesis of arylglycine derivatives by cationic palladium(ll)-catalyzed addition of arylboronic acids to N-tert-butanesulfinyl imino esters
A cationic palladium-complex-catalyzed addition of arylboronic acids to N-tert-butanesulfinyl iminoacetates to yield the optically active arylglycine derivatives with moderate to good yield and high diastereoselectivity was developed. This reaction provid
Dai, Huixiong,Lu, Xiyan
p. 3077 - 3080
(2008/02/11)
Reaction of organolead triacetates with 4-ethoxycarbonyl-2-methyl-4,5-dihydro-1,3-oxazol-5-one. The synthesis of α-aryl- and α-vinyl-N-acetylglycines and their ethyl esters and their enzymic resolution
4-Ethoxycarbonyl-2-methyl-4,5-dihydro-1,3-oxazol-5-one 7, which may be readily obtained from diethyl acetamidomalonate, undergoes high-yielding arylation and vinylation at the 4-position with organolead triacetates to give compounds which may be hydrolysed to give either the α-aryl- or α-vinyl-N-acetylglycine or the corresponding ethyl ester. The kinetic resolution of a number of these derivatives by enzymic hydrolysis of either the amide or ester function has been demonstrated.
Morgan, Jacqueline,Pinhey, John T.,Sherry, Christopher J.
p. 613 - 619
(2007/10/03)
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