Organocatalysis using protonated 1,2-diamino-1,2-diphenylethane for asymmetric Diels-Alder reaction

Kyoung Hoon Kim, Seil Lee, Dae Woong Lee, Dong Hyun Ko, Deok-Chan Ha

Research output: Contribution to journalArticle

52 Citations (Scopus)

Abstract

Bisammonium salts of mono-N-alkylated chiral 1,2-diamino-1,2-diphenylethane (DPEN) were employed in the catalytic and asymmetric Diels-Alder reaction between cyclopentadiene and crotonaldehyde. The N-3-pentyl diamine·2HCl catalyst shows high endo/exo selectivity and endo-enantioselectivity for the cycloaddition, and this organocatalysis is the first example of the use of a chiral 1,2-diamine to generate an imine intermediate which is activated by an internal ammonium Brønsted acid for the cycloaddition in a wet solvent.

Original languageEnglish
Pages (from-to)5991-5994
Number of pages4
JournalTetrahedron Letters
Volume46
Issue number36
DOIs
Publication statusPublished - 2005 Sep 5

Fingerprint

2-butenal
Cycloaddition
Cycloaddition Reaction
Cyclopentanes
Imines
Diamines
Catalyst selectivity
Enantioselectivity
Ammonium Compounds
Salts
Catalysts
Acids
meso-1,2-diphenylethylenediamine

Keywords

  • Aldehydes
  • Ammonium salts
  • Asymmetric Diels-Alder
  • Cyclopentadiene
  • Organocatalysis

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Organocatalysis using protonated 1,2-diamino-1,2-diphenylethane for asymmetric Diels-Alder reaction. / Kim, Kyoung Hoon; Lee, Seil; Lee, Dae Woong; Ko, Dong Hyun; Ha, Deok-Chan.

In: Tetrahedron Letters, Vol. 46, No. 36, 05.09.2005, p. 5991-5994.

Research output: Contribution to journalArticle

Kim, Kyoung Hoon ; Lee, Seil ; Lee, Dae Woong ; Ko, Dong Hyun ; Ha, Deok-Chan. / Organocatalysis using protonated 1,2-diamino-1,2-diphenylethane for asymmetric Diels-Alder reaction. In: Tetrahedron Letters. 2005 ; Vol. 46, No. 36. pp. 5991-5994.
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