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

  • 발행 : 2005.06.20

초록

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.

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참고문헌

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  2. Dynamic Kinetic Resolution of α-Bromo Carboxylic Acid Derivatives in Asymmetric Nucleophilic Substitution with Chiral α-Amino Esters. vol.36, pp.47, 2005, https://doi.org/10.1002/chin.200547190
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  7. Dynamic resolution of α-halo carboxylic acid derivatives in asymmetric nucleophilic substitution using chiral auxiliaries vol.20, pp.21, 2005, https://doi.org/10.1016/j.tetasy.2009.10.014
  8. Efficient Assembly of Iminodicarboxamides by a “Truly” Four‐Component Reaction vol.124, pp.41, 2005, https://doi.org/10.1002/ange.201205366
  9. Efficient Assembly of Iminodicarboxamides by a “Truly” Four‐Component Reaction vol.51, pp.41, 2005, https://doi.org/10.1002/anie.201205366