Design and Synthesis of Chiral Lewis Acid Catalysts for Aqueous Diels-Aider and Barbier Reactions

Authors

  • Susan D. Arco Institute of Chemistry/Natural Sciences Research Institute, College of Science, University of the Philippines Diliman, Quezon City
  • Jonathan T. Miranda Natural Sciences Research Institute, College of Science, University of the Philippines Diliman, Quezon City

DOI:

https://doi.org/10.26534/kimika.v22i1.33-42

Keywords:

Lewis acids, chiral, enantioselectivity, stereoselectivity, binaphthol, aqueous media, Diels-Alder, Barbier, lanthanide

Abstract

We report here the successful synthesis of two 3, 3' -difluorenyl binaphthols. In the divergent strategy employed in the synthesis, the 3,3' and 2,2'-positionsof (S)-(-)-1,1'-binaphthol were brominated and methylated, respectively, leading to the formation of a product that can be converted to a Grignard reagent. A Grignard addition to 9-fluorenone followed by deprotection afforded the target compounds. We also present here the method of testing their utility as ligands in chiral Lewis acid-catalyzed aqueous Barbier and Diels-Alder methodologies. The chiral Lewis acid complexes (CLAC) were generated in situ by mixing lanthanide triflates and 3,3'binaphthol derivatives. Among the six lanthanide triflates tested, only the Yb(OTf)3 -3,3'binaphtol derivative complex showed promising results for both model reactions.

Downloads

Published

2006-04-01

How to Cite

Arco, S. D., & Miranda, J. T. (2006). Design and Synthesis of Chiral Lewis Acid Catalysts for Aqueous Diels-Aider and Barbier Reactions. KIMIKA, 22(1), 33–42. https://doi.org/10.26534/kimika.v22i1.33-42

Issue

Vol. 22 No. 1 (2006)

Section

Research Articles

License

Authors who publish with this journal agree to the following terms:

  1. Authors retain copyright and grant the journal right of first publication with the work simultaneously licensed under a Creative Commons Attribution License that allows others to share the work with an acknowledgement of the work's authorship and initial publication in this journal.
  2. Authors are able to enter into separate, additional contractual arrangements for the non-exclusive distribution of the journal's published version of the work (e.g., post it to an institutional repository or publish it in a book), with an acknowledgement of its initial publication in this journal.
  3. Authors are permitted and encouraged to post their work online (e.g., in institutional repositories or on their website) prior to and during the submission process, as it can lead to productive exchanges, as well as earlier and greater citation of published work (See The Effect of Open Access).