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1 article(s) from Schörgenhumer, Johannes

Chiral phase-transfer catalysis in the asymmetric α-heterofunctionalization of prochiral nucleophiles

Johannes Schörgenhumer,
Maximilian Tiffner and
Mario Waser

Beilstein J. Org. Chem. 2017, 13, 1753–1769, doi:10.3762/bjoc.13.170

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Graphical Abstract

Scheme 1: Generally accepted ion-pairing mechanism between the chiral cation Q⁺ of a PTC and an enolate and s...

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Scheme 2: Reported asymmetric α-fluorination of β-ketoesters 1 using different chiral PTCs.

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Scheme 3: Asymmetric α-fluorination of benzofuranones 4 with phosphonium salt PTC F1.

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Scheme 4: Asymmetric α-fluorination of 1 with chiral phosphate-based catalysts.

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Scheme 5: Anionic PTC-catalysed α-fluorination of enamines 7 and ketones 10.

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Scheme 6: PTC-catalysed α-chlorination reactions of β-ketoesters 1.

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Scheme 7: Shioiri’s seminal report of the asymmetric α-hydroxylation of 15 with chiral ammonium salt PTCs.

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Scheme 8: Asymmetric ammonium salt-catalysed α-hydroxylation using oxygen together with a P(III)-based reduct...

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Scheme 9: Asymmetric ammonium salt-catalysed α-photooxygenations.

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Scheme 10: Asymmetric ammonium salt-catalysed α-hydroxylations using organic oxygen-transfer reagents.

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Scheme 11: Asymmetric triazolium salt-catalysed α-hydroxylation with in situ generated peroxy imidic acid 24.

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Scheme 12: Phase-transfer-catalysed dearomatization of phenols and naphthols.

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Scheme 13: Ishihara’s ammonium salt-catalysed oxidative cycloetherification.

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Scheme 14: Chiral phase-transfer-catalysed α-sulfanylation reactions.

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Scheme 15: Chiral phase-transfer-catalysed α-trifluoromethylthiolation of β-ketoesters 1.

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Scheme 16: Chiral phase-transfer-catalysed α-amination of β-ketoesters 1 using diazocarboxylates 38.

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Scheme 17: Asymmetric α-fluorination of benzofuranones 4 using diazocarboxylates 38 in the presence of phospho...

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Scheme 18: Anionic phase-transfer-catalysed α-amination of β-ketoesters 1 with aryldiazonium salts 41.

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Scheme 19: Triazolium salt L-catalysed α-amination of different prochiral nucleophiles with in situ activated ...

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Scheme 20: Phase-transfer-catalysed Neber rearrangement.

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Review

Published 22 Aug 2017

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