Evaluating the use of chiral anthracene templates to access pyroglutamic acids

Research output: Contribution to journalArticle

14 Citations (Scopus)

Abstract

An approach for the asymmetric synthesis of pyroglutamic acid derivatives is described based on an anthracene chiral auxiliary. The introduction of a furan ring as a masked carboxylic acid moiety proceeded with excellent levels of diastereo-selectivity, followed by conversion into a carboxylate ester. The ensuing retro-Diels-Alder procedure using flash vacuum pyrolysis (FVP) followed by reduction gave pyroglutamate esters in good yield but poor enantioselectivity, the latter of which was found to be dependant on the electronic nature of the N-protecting group.

Original languageEnglish
Pages (from-to)2719-2725
Number of pages7
JournalTetrahedron Asymmetry
Volume21
Issue number21-22
DOIs
Publication statusPublished - 25 Nov 2010
Externally publishedYes

Fingerprint

Pyrrolidonecarboxylic Acid
Anthracene
anthracene
esters
Esters
templates
acids
Acids
Enantioselectivity
furans
Carboxylic Acids
Carboxylic acids
carboxylic acids
carboxylates
pyrolysis
flash
Pyrolysis
selectivity
Vacuum
Derivatives

ASJC Scopus subject areas

  • Organic Chemistry
  • Inorganic Chemistry
  • Physical and Theoretical Chemistry
  • Catalysis

Cite this

Evaluating the use of chiral anthracene templates to access pyroglutamic acids. / Hasbullah, Siti Aishah; Jones, Simon.

In: Tetrahedron Asymmetry, Vol. 21, No. 21-22, 25.11.2010, p. 2719-2725.

Research output: Contribution to journalArticle

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