Bulletin of the Korean Chemical Society

  • 제26권6호
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  • Pages.989-992
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  • 2005
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  • 0253-2964(pISSN)
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  • 1229-5949(eISSN)
대한화학회 (Korean Chemical Society)
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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
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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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피인용 문헌

  1. L-Lactate-mediated Dynamic Kinetic Resolution of α-Bromo Esters for Asymmetric Syntheses of α-Amino Acid Derivatives vol.34, pp.8, 2013, https://doi.org/10.5012/bkcs.2013.34.8.2531
  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
  3. Stereoselective Preparation of N-Alkyl Dipeptide Analogues via Dynamic Kinetic Resolution of α-Halo Acyl Amino Esters vol.27, pp.3, 2006, https://doi.org/10.5012/bkcs.2006.27.3.447
  4. N-Methyl Pseudoephedrine-mediated Asymmetric Syntheses of Dihydroquinoxalinones for the Preparation of Flavane Analogues vol.28, pp.2, 2005, https://doi.org/10.5012/bkcs.2007.28.2.325
  5. Diacetone-D-glucose-mediated Asymmetric Syntheses of N-Carboxyalkylated and O-Carboxyalkylated Flavones vol.28, pp.7, 2007, https://doi.org/10.5012/bkcs.2007.28.7.1199
  6. Asymmetric Dehydration of β -Styryl- β -hydroxy Esters and Application to the Synthesis of a Neoflavonoid vol.29, pp.4, 2005, https://doi.org/10.5012/bkcs.2008.29.4.859
  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