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

Abstract

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.�⨀ԀĀ衺�⨀ԀĀऐ돀졽�⨀堘�⨀ꢐ�⨀돐좐�⨀��⨀킐�⨀뤏덐�⨀렏頏࢑�⨀਀࢑�⨀ᢑ�⨀؀ကᢑ�⨀?麆Ѐက䂑�⨀䂑�⨀