Display options
Cite
Reddy Guduru SK, Chamakuri S, Raji IO, et al. Synthesis of Enantiomerically Pure 3-Substituted Piperazine-2-acetic Acid Esters as Intermediates for Library Production. J Org Chem. 2018;83(19):11777-11793doi: 10.1021/acs.joc.8b01708.
Reddy Guduru, S. K., Chamakuri, S., Raji, I. O., MacKenzie, K. R., Santini, C., & Young, D. W. (2018). Synthesis of Enantiomerically Pure 3-Substituted Piperazine-2-acetic Acid Esters as Intermediates for Library Production. The Journal of organic chemistry, 83(19), 11777-11793. https://doi.org/10.1021/acs.joc.8b01708
Reddy Guduru, Shiva Krishna, et al. "Synthesis of Enantiomerically Pure 3-Substituted Piperazine-2-acetic Acid Esters as Intermediates for Library Production." The Journal of organic chemistry vol. 83,19 (2018): 11777-11793. doi: https://doi.org/10.1021/acs.joc.8b01708
Reddy Guduru SK, Chamakuri S, Raji IO, MacKenzie KR, Santini C, Young DW. Synthesis of Enantiomerically Pure 3-Substituted Piperazine-2-acetic Acid Esters as Intermediates for Library Production. J Org Chem. 2018 Oct 05;83(19):11777-11793. doi: 10.1021/acs.joc.8b01708. Epub 2018 Sep 18. PMID: 30180575.
Copy Download .nbib Format: NLM
Share it on

J Org Chem. 2018 Oct 05;83(19):11777-11793. doi: 10.1021/acs.joc.8b01708. Epub 2018 Sep 18.

Synthesis of Enantiomerically Pure 3-Substituted Piperazine-2-acetic Acid Esters as Intermediates for Library Production.

The Journal of organic chemistry

Shiva Krishna Reddy Guduru, Srinivas Chamakuri, Idris O Raji, Kevin R MacKenzie, Conrad Santini, Damian W Young

Affiliations

  1. Center for Drug Discovery , Baylor College of Medicine , One Baylor Plaza , Houston , Texas 77030 , United States.
  2. Department of Pharmacology and Chemical Biology , Baylor College of Medicine , One Baylor Plaza , Houston , Texas 77030 , United States.
  3. Department of Pathology and Immunology , Baylor College of Medicine , One Baylor Plaza , Houston , Texas 77030 , United States.

PMID: 30180575 DOI: 10.1021/acs.joc.8b01708

Abstract

The piperazine heterocycle is broadly exploited in FDA-approved drugs and biologically active compounds, but its chemical diversity is usually limited to ring nitrogen substitutions, leaving the four carbon atoms underutilized. Using an efficient six-step synthesis, chiral amino acids were transformed into 3-substituted piperazine-2-acetic acid esters as diastereomeric mixtures whose cis and trans products (dr 0.56 → 2.2:1, respectively) could be chromatographically separated. From five amino acids (both antipodes) was obtained a complete matrix of 20 monoprotected chiral 2,3-disubstituted piperazines, each as a single absolute stereoisomer, all but one in multigram quantities. In keeping with our overall purpose of constructing more Csp

Publication Types