3-Pyrroline-1-carbonyl (Pyroc) group

A removable protecting group for the kinetic resolution of racemic carboxylic acids and alcohols through catalytic asymmetric acylation

Akira Sakakura, Shuhei Umemura, Kazuaki Ishihara

Research output: Contribution to journalArticle

19 Citations (Scopus)

Abstract

The O-3-pyrroline-1-carbonyl (O-Pyroc) group and 3-pyrrolinamide are useful removable protecting groups for the kinetic resolution of racemic α-hydroxycarboxylic acids, β-hydroxycarboxylic acids, 1,2-dicarboxylic acids, and 1,2-diols using the L-histidine-derived bifunctional catalysts. The Pyroc group can be easily introduced from Pyroc chloride. Selective deprotection of the Pyroc group and 3-pyrrolinamide can be carried out via DDQ oxidation followed by hydrolysis using sodium hydroxide, without epimerization.

Original languageEnglish
Pages (from-to)1647-1650
Number of pages4
JournalSynlett
Issue number10
DOIs
Publication statusPublished - Jun 2009
Externally publishedYes

Fingerprint

Acylation
Carboxylic Acids
Alcohols
Kinetics
Dicarboxylic Acids
Sodium Hydroxide
Acids
Histidine
Chlorides
Hydrolysis
Oxidation
Catalysts
pyrroline

Keywords

  • 3-pyrroline-1-carbonyl (Pyroc)
  • Asymmetric acylation
  • Kinetic resolution
  • L-histidine framework
  • Protective and removable

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

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abstract = "The O-3-pyrroline-1-carbonyl (O-Pyroc) group and 3-pyrrolinamide are useful removable protecting groups for the kinetic resolution of racemic α-hydroxycarboxylic acids, β-hydroxycarboxylic acids, 1,2-dicarboxylic acids, and 1,2-diols using the L-histidine-derived bifunctional catalysts. The Pyroc group can be easily introduced from Pyroc chloride. Selective deprotection of the Pyroc group and 3-pyrrolinamide can be carried out via DDQ oxidation followed by hydrolysis using sodium hydroxide, without epimerization.",
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author = "Akira Sakakura and Shuhei Umemura and Kazuaki Ishihara",
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journal = "Synlett",
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T2 - A removable protecting group for the kinetic resolution of racemic carboxylic acids and alcohols through catalytic asymmetric acylation

AU - Sakakura, Akira

AU - Umemura, Shuhei

AU - Ishihara, Kazuaki

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AB - The O-3-pyrroline-1-carbonyl (O-Pyroc) group and 3-pyrrolinamide are useful removable protecting groups for the kinetic resolution of racemic α-hydroxycarboxylic acids, β-hydroxycarboxylic acids, 1,2-dicarboxylic acids, and 1,2-diols using the L-histidine-derived bifunctional catalysts. The Pyroc group can be easily introduced from Pyroc chloride. Selective deprotection of the Pyroc group and 3-pyrrolinamide can be carried out via DDQ oxidation followed by hydrolysis using sodium hydroxide, without epimerization.

KW - 3-pyrroline-1-carbonyl (Pyroc)

KW - Asymmetric acylation

KW - Kinetic resolution

KW - L-histidine framework

KW - Protective and removable

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