Isatin derivatives are reactive electrophilic components for the Baylis-Hillman reaction

Simon J Garden, Jan Skakle

Research output: Contribution to journalArticle

50 Citations (Scopus)

Abstract

Isatin derivatives readily react as the electrophilic component in the Baylis-Hillman reaction giving good to excellent yields of the respective adducts. It is generally accepted that ketones only take part in the Baylis-Hillman reaction under relatively extreme conditions. with a few exceptions. Isatin on the other hand readily reacts with acrylic acid derivatives in ethanol and or ethanol/THF mixtures in the presence of a catalytic quantity of DABCO. The solid state structures for these novel dioxindole derivatives were determined for two adducts by single-crystal X-ray diffraction spectroscopy, revealing an inside hydroxyl conformation (C) 2002 Elsevier Science Ltd. All rights reserved.

Original languageEnglish
Pages (from-to)1969-1972
Number of pages4
JournalTetrahedron Letters
Volume43
Issue number11
Early online date1 Feb 2002
DOIs
Publication statusPublished - 11 Mar 2002

Keywords

  • alpha-keto esters
  • asymmetric-synthesis
  • methyl acrylate
  • acrylonitrile
  • methodology
  • adducts

Cite this

Isatin derivatives are reactive electrophilic components for the Baylis-Hillman reaction. / Garden, Simon J ; Skakle, Jan.

In: Tetrahedron Letters, Vol. 43, No. 11, 11.03.2002, p. 1969-1972.

Research output: Contribution to journalArticle

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AB - Isatin derivatives readily react as the electrophilic component in the Baylis-Hillman reaction giving good to excellent yields of the respective adducts. It is generally accepted that ketones only take part in the Baylis-Hillman reaction under relatively extreme conditions. with a few exceptions. Isatin on the other hand readily reacts with acrylic acid derivatives in ethanol and or ethanol/THF mixtures in the presence of a catalytic quantity of DABCO. The solid state structures for these novel dioxindole derivatives were determined for two adducts by single-crystal X-ray diffraction spectroscopy, revealing an inside hydroxyl conformation (C) 2002 Elsevier Science Ltd. All rights reserved.

KW - alpha-keto esters

KW - asymmetric-synthesis

KW - methyl acrylate

KW - acrylonitrile

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