Syntheses of arabinose-derived pyrrolidine catalysts and their applications in intramolecular Diels-Alder reactions

Tony Kung Ming Shing, Kwun W. Wu, Ho T. Wu, Qicai Xiao

Research output: Contribution to journalArticle

3 Citations (Scopus)

Abstract

Six chiral hydroxylated pyrrolidine catalysts were synthesized from commercially available D-arabinose in seven steps. Various aromatic substituents α to the amine can be introduced readily by a Grignard reaction, which enables facile optimization of the catalyst performance. The stereoselectivities of these catalysts have been assessed by comparing with those of MacMillan's imidazolidinone in a known intramolecular Diels-Alder (IMDA) reaction of a triene. Two additional IMDA reactions of symmetrical dienals with concomitant desymmetrisation further established the potential use of these novel amine catalysts. These pyrrolidines are valuable catalysts for other synthetic transformations.

Original languageEnglish
Pages (from-to)1754-1762
Number of pages9
JournalOrganic and Biomolecular Chemistry
Volume13
Issue number6
DOIs
Publication statusPublished - 2015 Feb 14
Externally publishedYes

Fingerprint

Diels-Alder reactions
Arabinose
Cycloaddition Reaction
Amines
Pyrrolidines
catalysts
Catalysts
synthesis
amines
Grignard reactions
trienes
Stereoselectivity
pyrrolidine
optimization

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Syntheses of arabinose-derived pyrrolidine catalysts and their applications in intramolecular Diels-Alder reactions. / Shing, Tony Kung Ming; Wu, Kwun W.; Wu, Ho T.; Xiao, Qicai.

In: Organic and Biomolecular Chemistry, Vol. 13, No. 6, 14.02.2015, p. 1754-1762.

Research output: Contribution to journalArticle

Shing, Tony Kung Ming ; Wu, Kwun W. ; Wu, Ho T. ; Xiao, Qicai. / Syntheses of arabinose-derived pyrrolidine catalysts and their applications in intramolecular Diels-Alder reactions. In: Organic and Biomolecular Chemistry. 2015 ; Vol. 13, No. 6. pp. 1754-1762.
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