Aminocatalytic [8+2] Cycloaddition Reactions toward Chiral Cyclazines

Nicolaj Inunnguaq Jessen; Maksimilian Bura; Giulio Bertuzzi; Karl Anker Jørgensen

doi:10.1002/anie.202106287

Aminocatalytic [8+2] Cycloaddition Reactions toward Chiral Cyclazines

Nicolaj Inunnguaq Jessen, Maksimilian Bura, Giulio Bertuzzi, Karl Anker Jørgensen^*

^*Corresponding author for this work

Department of Chemistry

Research output: Contribution to journal/Conference contribution in journal/Contribution to newspaper › Journal article › Research › peer-review

Abstract

An efficient and exceptionally stereoselective synthesis of chiral cycl[3.2.2]azines has been realized by means of the rational design and utilization of novel (E)-3-benzylidene-3H-pyrrolizines in iminium-ion-catalyzed [8+2] cycloaddition reactions. The presented protocol allows for the incorporation of diverse enals, including cinnamaldehydes, enolizable aldehydes, and substrates of extended conjugation. The obtained products contain both an electron-rich alkenyl pyrrole moiety and an electron-deficient carbaldehyde substituent, and both moieties can undergo selective transformations with retention of the stereochemical information established in the [8+2] cycloaddition.

Original language	English
Journal	Angewandte Chemie International Edition
Volume	60
Issue	34
Pages (from-to)	18527-18531
Number of pages	5
ISSN	1433-7851
DOIs	https://doi.org/10.1002/anie.202106287
Publication status	Published - 16 Aug 2021

Keywords

asymmetric synthesis
cycloaddition
fused-ring systems
nitrogen heterocycles
organocatalysis
ALKALOIDS

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10.1002/anie.202106287

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title = "Aminocatalytic [8+2] Cycloaddition Reactions toward Chiral Cyclazines",

abstract = "An efficient and exceptionally stereoselective synthesis of chiral cycl[3.2.2]azines has been realized by means of the rational design and utilization of novel (E)-3-benzylidene-3H-pyrrolizines in iminium-ion-catalyzed [8+2] cycloaddition reactions. The presented protocol allows for the incorporation of diverse enals, including cinnamaldehydes, enolizable aldehydes, and substrates of extended conjugation. The obtained products contain both an electron-rich alkenyl pyrrole moiety and an electron-deficient carbaldehyde substituent, and both moieties can undergo selective transformations with retention of the stereochemical information established in the [8+2] cycloaddition.",

keywords = "asymmetric synthesis, cycloaddition, fused-ring systems, nitrogen heterocycles, organocatalysis, ALKALOIDS",

author = "Jessen, {Nicolaj Inunnguaq} and Maksimilian Bura and Giulio Bertuzzi and J{\o}rgensen, {Karl Anker}",

year = "2021",

month = aug,

day = "16",

doi = "10.1002/anie.202106287",

language = "English",

volume = "60",

pages = "18527--18531",

journal = "Angewandte Chemie International Edition",

issn = "1433-7851",

publisher = "Wiley - VCH Verlag GmbH & CO. KGaA",

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}

Aminocatalytic [8+2] Cycloaddition Reactions toward Chiral Cyclazines. / Jessen, Nicolaj Inunnguaq; Bura, Maksimilian; Bertuzzi, Giulio et al.
In: Angewandte Chemie International Edition, Vol. 60, No. 34, 16.08.2021, p. 18527-18531.

Research output: Contribution to journal/Conference contribution in journal/Contribution to newspaper › Journal article › Research › peer-review

TY - JOUR

T1 - Aminocatalytic [8+2] Cycloaddition Reactions toward Chiral Cyclazines

AU - Jessen, Nicolaj Inunnguaq

AU - Bura, Maksimilian

AU - Bertuzzi, Giulio

AU - Jørgensen, Karl Anker

PY - 2021/8/16

Y1 - 2021/8/16

N2 - An efficient and exceptionally stereoselective synthesis of chiral cycl[3.2.2]azines has been realized by means of the rational design and utilization of novel (E)-3-benzylidene-3H-pyrrolizines in iminium-ion-catalyzed [8+2] cycloaddition reactions. The presented protocol allows for the incorporation of diverse enals, including cinnamaldehydes, enolizable aldehydes, and substrates of extended conjugation. The obtained products contain both an electron-rich alkenyl pyrrole moiety and an electron-deficient carbaldehyde substituent, and both moieties can undergo selective transformations with retention of the stereochemical information established in the [8+2] cycloaddition.

AB - An efficient and exceptionally stereoselective synthesis of chiral cycl[3.2.2]azines has been realized by means of the rational design and utilization of novel (E)-3-benzylidene-3H-pyrrolizines in iminium-ion-catalyzed [8+2] cycloaddition reactions. The presented protocol allows for the incorporation of diverse enals, including cinnamaldehydes, enolizable aldehydes, and substrates of extended conjugation. The obtained products contain both an electron-rich alkenyl pyrrole moiety and an electron-deficient carbaldehyde substituent, and both moieties can undergo selective transformations with retention of the stereochemical information established in the [8+2] cycloaddition.

KW - asymmetric synthesis

KW - cycloaddition

KW - fused-ring systems

KW - nitrogen heterocycles

KW - organocatalysis

KW - ALKALOIDS

UR - http://www.scopus.com/inward/record.url?scp=85110436357&partnerID=8YFLogxK

U2 - 10.1002/anie.202106287

DO - 10.1002/anie.202106287

M3 - Journal article

C2 - 34101936

SN - 1433-7851

VL - 60

SP - 18527

EP - 18531

JO - Angewandte Chemie International Edition

JF - Angewandte Chemie International Edition

IS - 34

ER -

Aminocatalytic [8+2] Cycloaddition Reactions toward Chiral Cyclazines

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Keywords

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