An asymmetric organocatalytic aldol reaction of a hydrophobic aldehyde in aqueous medium running in flow mode

Lukas Schober, Shahilan Ratnam, Yasunobu Yamashita, Niklas Adebar, Matthias Pieper, Albrecht Berkessel, Volker Hessel, Harald Gröger (Corresponding author)

Research output: Contribution to journalArticleAcademicpeer-review

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Abstract

Reaction conditions have been identified to conduct a one-pot asymmetric organocatalytic aldol reaction with a hydrophobic substrate in aqueous medium via a process running in flow mode. By employing a mixture of water and 2-propanol, a hydrophobic aldehyde and 3.6 mol% of an organocatalyst, this microreactor process affords the desired aldol adduct with a conversion of 74% and an enantioselectivity of 89% after a reaction time of 60 minutes.

Original languageEnglish
Pages (from-to)1178-1184
Number of pages7
JournalSynthesis
Volume51
Issue number5
DOIs
Publication statusPublished - Mar 2019

Fingerprint

Enantioselectivity
Propanol
Aldehydes
2-Propanol
Substrates
Water
3-hydroxybutanal

Keywords

  • aldol reaction
  • asymmetric catalysis
  • continuously running processes
  • flow chemistry
  • organocatalysis
  • water

Cite this

Schober, L., Ratnam, S., Yamashita, Y., Adebar, N., Pieper, M., Berkessel, A., ... Gröger, H. (2019). An asymmetric organocatalytic aldol reaction of a hydrophobic aldehyde in aqueous medium running in flow mode. Synthesis, 51(5), 1178-1184. https://doi.org/10.1055/s-0037-1610404
Schober, Lukas ; Ratnam, Shahilan ; Yamashita, Yasunobu ; Adebar, Niklas ; Pieper, Matthias ; Berkessel, Albrecht ; Hessel, Volker ; Gröger, Harald. / An asymmetric organocatalytic aldol reaction of a hydrophobic aldehyde in aqueous medium running in flow mode. In: Synthesis. 2019 ; Vol. 51, No. 5. pp. 1178-1184.
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Schober, L, Ratnam, S, Yamashita, Y, Adebar, N, Pieper, M, Berkessel, A, Hessel, V & Gröger, H 2019, 'An asymmetric organocatalytic aldol reaction of a hydrophobic aldehyde in aqueous medium running in flow mode', Synthesis, vol. 51, no. 5, pp. 1178-1184. https://doi.org/10.1055/s-0037-1610404

An asymmetric organocatalytic aldol reaction of a hydrophobic aldehyde in aqueous medium running in flow mode. / Schober, Lukas; Ratnam, Shahilan; Yamashita, Yasunobu; Adebar, Niklas; Pieper, Matthias; Berkessel, Albrecht; Hessel, Volker; Gröger, Harald (Corresponding author).

In: Synthesis, Vol. 51, No. 5, 03.2019, p. 1178-1184.

Research output: Contribution to journalArticleAcademicpeer-review

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AU - Hessel, Volker

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KW - asymmetric catalysis

KW - continuously running processes

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KW - organocatalysis

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