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http://dx.doi.org/10.5012/bkcs.2005.26.6.989

Dynamic Kinetic Resolution of α-Bromo Carboxylic Acid Derivatives in Asymmetric Nucleophilic Substitution with Chiral α-Amino Esters  

Chang, Ji-Yeon (Department of Chemistry, Konkuk University)
Shin, Eun-Kyoung (Department of Chemistry, Konkuk University)
Kim, Hyun-Jung (Department of Chemistry, Konkuk University)
Kim, Yong-Tae (Department of Chemistry, Konkuk University)
Park, Yong-Sun (Department of Chemistry, Konkuk University)
Publication Information
Bulletin of the Korean Chemical Society / v.26, no.6, 2005 , pp. 989-992 More about this Journal
Abstract
Dynamic kinetic resolution of $\alpha$-bromo carboxylic acid derivatives in nucleophilic substitution with chiral $\alpha$-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 $\alpha$-amino esters gave iminodiacetates 2-8 with stereoselectivities up to 87 : 13 dr. Also, the reactions of N-($\alpha$-bromo-$\alpha$-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.
Keywords
Dynamic kinetic resolution; Asymmetric syntheses; Nucleophilic substitution;
Citations & Related Records
Times Cited By KSCI : 2  (Citation Analysis)
Times Cited By Web Of Science : 7  (Related Records In Web of Science)
Times Cited By SCOPUS : 6
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