Catalytic Enantioselective [10+4] Cycloadditions

Bjarke S. Donslund; Nicolaj Inunnguaq Jessen; Giulio Bertuzzi; Maxime Giardinetti; Teresa A. Palazzo; Mette Louise Christensen; Karl Anker Jørgensen

doi:10.1002/anie.201807830

Catalytic Enantioselective [10+4] Cycloadditions

Bjarke S. Donslund, Nicolaj Inunnguaq Jessen, Giulio Bertuzzi, Maxime Giardinetti, Teresa A. Palazzo, Mette Louise Christensen, 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

The first peri- and stereoselective [10+4] cycloaddition between catalytically generated amino isobenzofulvenes and electron-deficient dienes is described. The highly stereoselective catalytic [10+4] cycloaddition exhibits a broad scope with high yields, reflecting a robust higher-order cycloaddition. Experimental and computational investigations support a kinetic distribution of intermediate rotamers dictating the enantioselectivity, which relies heavily on additive effects.

Original language	English
Journal	Angewandte Chemie - International Edition
Volume	57
Issue	40
Pages (from-to)	13182-13186
Number of pages	5
ISSN	1433-7851
DOIs	https://doi.org/10.1002/anie.201807830
Publication status	Published - 1 Oct 2018

Keywords

asymmetric synthesis
cycloaddition
density-functional calculations
organocatalysis

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10.1002/anie.201807830

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title = "Catalytic Enantioselective [10+4] Cycloadditions",

abstract = "The first peri- and stereoselective [10+4] cycloaddition between catalytically generated amino isobenzofulvenes and electron-deficient dienes is described. The highly stereoselective catalytic [10+4] cycloaddition exhibits a broad scope with high yields, reflecting a robust higher-order cycloaddition. Experimental and computational investigations support a kinetic distribution of intermediate rotamers dictating the enantioselectivity, which relies heavily on additive effects.",

keywords = "asymmetric synthesis, cycloaddition, density-functional calculations, organocatalysis",

author = "Donslund, {Bjarke S.} and Jessen, {Nicolaj Inunnguaq} and Giulio Bertuzzi and Maxime Giardinetti and Palazzo, {Teresa A.} and Christensen, {Mette Louise} and J{\o}rgensen, {Karl Anker}",

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doi = "10.1002/anie.201807830",

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AU - Donslund, Bjarke S.

AU - Jessen, Nicolaj Inunnguaq

AU - Bertuzzi, Giulio

AU - Giardinetti, Maxime

AU - Palazzo, Teresa A.

AU - Christensen, Mette Louise

AU - Jørgensen, Karl Anker

PY - 2018/10/1

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N2 - The first peri- and stereoselective [10+4] cycloaddition between catalytically generated amino isobenzofulvenes and electron-deficient dienes is described. The highly stereoselective catalytic [10+4] cycloaddition exhibits a broad scope with high yields, reflecting a robust higher-order cycloaddition. Experimental and computational investigations support a kinetic distribution of intermediate rotamers dictating the enantioselectivity, which relies heavily on additive effects.

AB - The first peri- and stereoselective [10+4] cycloaddition between catalytically generated amino isobenzofulvenes and electron-deficient dienes is described. The highly stereoselective catalytic [10+4] cycloaddition exhibits a broad scope with high yields, reflecting a robust higher-order cycloaddition. Experimental and computational investigations support a kinetic distribution of intermediate rotamers dictating the enantioselectivity, which relies heavily on additive effects.

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KW - cycloaddition

KW - density-functional calculations

KW - organocatalysis

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U2 - 10.1002/anie.201807830

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EP - 13186

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 40

ER -

Catalytic Enantioselective [10+4] Cycloadditions

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Keywords

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