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

Bulletin of the Korean chemical society

Yong Sun Park¹  Hyun Jung Kim¹  Yongtae Kim¹  Eun-kyoung Shin¹  Ji-yeon Chang¹ 

关键词: Dynamic kinetic resolution;    Asymmetric syntheses;    Nucleophilic substitution;   

DOI  :  

学科分类：化学（综合）

来源: Korean Chemical Society

【 摘 要 】

Dynamic kinetic resolution of �?-bromo carboxylic acid derivatives in nucleophilic substitution with chiral �?- 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 �?-amino esters gave iminodiacetates 2-8 with stereoselectivities up to 87 : 13 dr. Also, the reactions of N-(�?-bromo-�?-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.

【 授权许可】

Unknown