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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 26, Number 6
BKCSDE 26(6)
June 20, 2005 

Dynamic Kinetic Resolution of α-Bromo Carboxylic Acid Derivatives in Asymmetric Nucleophilic Substitution with Chiral α-Amino Esters
Ji-yeon Chang, Eun-kyoung Shin, Hyun Jung Kim, Yongtae Kim, Yong Sun Park*
Dynamic kinetic resolution, Asymmetric syntheses, Nucleophilic substitution
Dynamic kinetic resolution of α-bromo carboxylic acid derivatives in nucleophilic substitution with chiral α- amino ester nucleophiles in the presence of TBAI and DIEA has been investigated for stereoselective syntheses of 1,1'-iminodicarboxylic acid derivatives. Nucleophilic substitutions with various chiral α-amino esters gave iminodiacetates 2-8 with stereoselectivities up to 87 : 13 dr. Also, the reactions of N-(α-bromo-α-phenylacetyl)-L-alanine methyl ester with L-alanine, D-alanine and glycine methyl ester nucleophiles afforded N-carboxyalkyl dipeptide analogues 10-12 up to 90 : 10 dr.
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