Experimental and computational study of the catalytic asymmetric 4π-electrocyclization of N-heterocycles

Sadiya Raja; Masaki Nakajima; Magnus Rueping

doi:10.1002/anie.201408020

Experimental and computational study of the catalytic asymmetric 4π-electrocyclization of N-heterocycles

Sadiya Raja, Masaki Nakajima, Magnus Rueping^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

45 Scopus citations

Abstract

The first asymmetric metal-catalyzed Nazarov cyclization of N-heterocycles has been developed. The use of a chiral catalyst allows the enantioselective electrocyclization of N-heterocycles under mild conditions and the corresponding products are obtained in good yields with excellent enantio- and diastereoselectivity. The reaction mechanism and the absolute configuration of the obtained products are explained by means of computational studies.

Original language	English (US)
Pages (from-to)	2762-2765
Number of pages	4
Journal	Angewandte Chemie - International Edition
Volume	54
Issue number	9
DOIs	https://doi.org/10.1002/anie.201408020
State	Published - Feb 23 2015
Externally published	Yes

Bibliographical note

Publisher Copyright:
© 2015 Wiley-VCH Verlag GmbH & Co. KGaA.

Keywords

Electrocyclization
Indole alkaloids
Lewis acid catalysis
Nazarov reaction

ASJC Scopus subject areas

Catalysis
General Chemistry

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10.1002/anie.201408020

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title = "Experimental and computational study of the catalytic asymmetric 4π-electrocyclization of N-heterocycles",

abstract = "The first asymmetric metal-catalyzed Nazarov cyclization of N-heterocycles has been developed. The use of a chiral catalyst allows the enantioselective electrocyclization of N-heterocycles under mild conditions and the corresponding products are obtained in good yields with excellent enantio- and diastereoselectivity. The reaction mechanism and the absolute configuration of the obtained products are explained by means of computational studies.",

keywords = "Electrocyclization, Indole alkaloids, Lewis acid catalysis, Nazarov reaction",

author = "Sadiya Raja and Masaki Nakajima and Magnus Rueping",

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AU - Raja, Sadiya

AU - Nakajima, Masaki

AU - Rueping, Magnus

PY - 2015/2/23

Y1 - 2015/2/23

N2 - The first asymmetric metal-catalyzed Nazarov cyclization of N-heterocycles has been developed. The use of a chiral catalyst allows the enantioselective electrocyclization of N-heterocycles under mild conditions and the corresponding products are obtained in good yields with excellent enantio- and diastereoselectivity. The reaction mechanism and the absolute configuration of the obtained products are explained by means of computational studies.

AB - The first asymmetric metal-catalyzed Nazarov cyclization of N-heterocycles has been developed. The use of a chiral catalyst allows the enantioselective electrocyclization of N-heterocycles under mild conditions and the corresponding products are obtained in good yields with excellent enantio- and diastereoselectivity. The reaction mechanism and the absolute configuration of the obtained products are explained by means of computational studies.

KW - Electrocyclization

KW - Indole alkaloids

KW - Lewis acid catalysis

KW - Nazarov reaction

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U2 - 10.1002/anie.201408020

DO - 10.1002/anie.201408020

M3 - Article

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AN - SCOPUS:84923091684

SN - 1433-7851

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JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 9

ER -

Experimental and computational study of the catalytic asymmetric 4π-electrocyclization of N-heterocycles

Abstract

Bibliographical note

Keywords

ASJC Scopus subject areas

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