Atroposelective Nenitzescu Indole Synthesis

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Abstract: In the past decade, compounds bearing a stereogenic C−N axis have gained significant attention in fields ranging from ligand to drug design. Yet, the atroposelective synthesis of these molecules remains a considerable challenge. In contrast to recent methods using more advanced chiral catalysts, a very simply accessed Jacobsen‐type chromium (III)−salen complex was used here as a chiral enantiopure Lewis acid catalyst for a highly atroposelective Nenitzescu indole synthesis. Mild reaction conditions afforded various 5‐hydroxybenzo[g]indoles in up to 97 % yield. Moreover, through a simple work‐up, very high enantiomeric excesses of up to 99 % could be obtained.

Location: Deutsche Nationalbibliothek Frankfurt am Main

Extent: Online-Ressource

Language: Englisch

Bibliographic citation: Atroposelective Nenitzescu Indole Synthesis ; day:08 ; month:03 ; year:2023 ; extent:7
Chemistry - a European journal ; (08.03.2023) (gesamt 7)

Creator: Thönnißen, Vinzenz
Atodiresei, Iuliana L.
Patureau, Frederic W.

DOI: 10.1002/chem.202300279

URN: urn:nbn:de:101:1-2023030914160008813963

Rights: Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.

Last update: 14.08.2025, 11:03 AM CEST

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Associated

Thönnißen, Vinzenz
Atodiresei, Iuliana L.
Patureau, Frederic W.

Other Objects (12)

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Total Synthesis of Indole Alkaloids

Total Synthesis of Indole Alkaloids

MODIFICATION OF THE FISCHER INDOLE SYNTHESIS.

MODIFICATION OF THE FISCHER INDOLE SYNTHESIS.

Total Synthesis of Seven Indole Alkaloids

Total Synthesis of Seven Indole Alkaloids

Biogenetically Inspired Synthesis of Indole Alkaloids

Biogenetically Inspired Synthesis of Indole Alkaloids

Construction of Spirocyclic Oxindoles for Indole Alkaloid Synthesis

Construction of Spirocyclic Oxindoles for Indole Alkaloid Synthesis

Synthesis of the Indole Core of MK-3281

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Step and redox efficient nitroarene to indole synthesis

Step and redox efficient nitroarene to indole synthesis

A MECHANISTIC DEVIATION IN THE BISCHLER INDOLE SYNTHESIS

A MECHANISTIC DEVIATION IN THE BISCHLER INDOLE SYNTHESIS

FISCHER INDOLE SYNTHESIS IN THE ABSENCE OF A SOLVENT

FISCHER INDOLE SYNTHESIS IN THE ABSENCE OF A SOLVENT

Larock Indole Synthesis

Larock Indole Synthesis

Atroposelective nenitzescu indole synthesis

Atroposelective nenitzescu indole synthesis

The Bartoli Indole Synthesis

The Bartoli Indole Synthesis

Total Synthesis of Indole Alkaloids

Total Synthesis of Indole Alkaloids

MODIFICATION OF THE FISCHER INDOLE SYNTHESIS.

MODIFICATION OF THE FISCHER INDOLE SYNTHESIS.

Total Synthesis of Seven Indole Alkaloids

Total Synthesis of Seven Indole Alkaloids

Biogenetically Inspired Synthesis of Indole Alkaloids

Biogenetically Inspired Synthesis of Indole Alkaloids

Construction of Spirocyclic Oxindoles for Indole Alkaloid Synthesis

Construction of Spirocyclic Oxindoles for Indole Alkaloid Synthesis

Synthesis of the Indole Core of MK-3281

Synthesis of the Indole Core of MK-3281

Step and redox efficient nitroarene to indole synthesis

Step and redox efficient nitroarene to indole synthesis

A MECHANISTIC DEVIATION IN THE BISCHLER INDOLE SYNTHESIS

A MECHANISTIC DEVIATION IN THE BISCHLER INDOLE SYNTHESIS

FISCHER INDOLE SYNTHESIS IN THE ABSENCE OF A SOLVENT

FISCHER INDOLE SYNTHESIS IN THE ABSENCE OF A SOLVENT

Larock Indole Synthesis

Larock Indole Synthesis

Atroposelective nenitzescu indole synthesis

Atroposelective nenitzescu indole synthesis

The Bartoli Indole Synthesis

The Bartoli Indole Synthesis

Total Synthesis of Indole Alkaloids

Total Synthesis of Indole Alkaloids

MODIFICATION OF THE FISCHER INDOLE SYNTHESIS.

MODIFICATION OF THE FISCHER INDOLE SYNTHESIS.

Total Synthesis of Seven Indole Alkaloids

Total Synthesis of Seven Indole Alkaloids

Biogenetically Inspired Synthesis of Indole Alkaloids

Biogenetically Inspired Synthesis of Indole Alkaloids

Construction of Spirocyclic Oxindoles for Indole Alkaloid Synthesis

Construction of Spirocyclic Oxindoles for Indole Alkaloid Synthesis

Synthesis of the Indole Core of MK-3281

Synthesis of the Indole Core of MK-3281

Step and redox efficient nitroarene to indole synthesis

Step and redox efficient nitroarene to indole synthesis

A MECHANISTIC DEVIATION IN THE BISCHLER INDOLE SYNTHESIS

A MECHANISTIC DEVIATION IN THE BISCHLER INDOLE SYNTHESIS

FISCHER INDOLE SYNTHESIS IN THE ABSENCE OF A SOLVENT

FISCHER INDOLE SYNTHESIS IN THE ABSENCE OF A SOLVENT

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