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

doi:10.1055/s-0037-1610404

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)

Micro Flow Chemistry and Synthetic Methodology

Research output: Contribution to journal › Article › Academic › peer-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 language	English
Pages (from-to)	1178-1184
Number of pages	7
Journal	Synthesis
Volume	51
Issue number	5
DOIs	https://doi.org/10.1055/s-0037-1610404
Publication status	Published - Mar 2019

Keywords

aldol reaction
asymmetric catalysis
continuously running processes
flow chemistry
organocatalysis
water

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10.1055/s-0037-1610404

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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.",

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T1 - An asymmetric organocatalytic aldol reaction of a hydrophobic aldehyde in aqueous medium running in flow mode

AU - Schober, Lukas

AU - Ratnam, Shahilan

AU - Yamashita, Yasunobu

AU - Adebar, Niklas

AU - Pieper, Matthias

AU - Berkessel, Albrecht

AU - Hessel, Volker

AU - Gröger, Harald

PY - 2019/3

Y1 - 2019/3

N2 - 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.

AB - 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.

KW - aldol reaction

KW - asymmetric catalysis

KW - continuously running processes

KW - flow chemistry

KW - organocatalysis

KW - water

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EP - 1184

JO - Synthesis

JF - Synthesis

SN - 0039-7881

IS - 5

ER -

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

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Keywords

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