Organocatalytic Enantioselective 1,3-Dipolar [6+4] Cycloadditions of Tropone

Giulio Bertuzzi; David McLeod; Lisa Marie Mohr; Karl Anker Jørgensen

doi:10.1002/chem.202003329

Organocatalytic Enantioselective 1,3-Dipolar [6+4] Cycloadditions of Tropone

Giulio Bertuzzi, David McLeod, Lisa Marie Mohr, 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

A highly stereoselective 1,3-dipolar [6+4] cycloaddition towards bridged azabicyclo[4.3.1]decane scaffolds has been developed, reacting aldehydes, 2-aminomalonates and tropone under mild conditions in the presence of a chiral phosphoric acid catalyst. The scope is demonstrated for a series of aldehydes and 2-aminomalonates, and the reaction proceeds in high yields, >95:5 d.r. and up to 99 % ee. A series of transformations, as well as a mechanistic proposal, are presented.

Original language	English
Journal	Chemistry - A European Journal
Volume	26
Issue	67
Pages (from-to)	15491-15496
Number of pages	6
ISSN	0947-6539
DOIs	https://doi.org/10.1002/chem.202003329
Publication status	Published - Dec 2020

Keywords

1,3-dipole
chiral phosphoric acids
enantioselectivity
higher-order cycloadditions
tropone

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10.1002/chem.202003329

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title = "Organocatalytic Enantioselective 1,3-Dipolar [6+4] Cycloadditions of Tropone",

abstract = "A highly stereoselective 1,3-dipolar [6+4] cycloaddition towards bridged azabicyclo[4.3.1]decane scaffolds has been developed, reacting aldehydes, 2-aminomalonates and tropone under mild conditions in the presence of a chiral phosphoric acid catalyst. The scope is demonstrated for a series of aldehydes and 2-aminomalonates, and the reaction proceeds in high yields, >95:5 d.r. and up to 99 % ee. A series of transformations, as well as a mechanistic proposal, are presented.",

keywords = "1,3-dipole, chiral phosphoric acids, enantioselectivity, higher-order cycloadditions, tropone",

author = "Giulio Bertuzzi and David McLeod and Mohr, {Lisa Marie} and J{\o}rgensen, {Karl Anker}",

year = "2020",

month = dec,

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volume = "26",

pages = "15491--15496",

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T1 - Organocatalytic Enantioselective 1,3-Dipolar [6+4] Cycloadditions of Tropone

AU - Bertuzzi, Giulio

AU - McLeod, David

AU - Mohr, Lisa Marie

AU - Jørgensen, Karl Anker

PY - 2020/12

Y1 - 2020/12

N2 - A highly stereoselective 1,3-dipolar [6+4] cycloaddition towards bridged azabicyclo[4.3.1]decane scaffolds has been developed, reacting aldehydes, 2-aminomalonates and tropone under mild conditions in the presence of a chiral phosphoric acid catalyst. The scope is demonstrated for a series of aldehydes and 2-aminomalonates, and the reaction proceeds in high yields, >95:5 d.r. and up to 99 % ee. A series of transformations, as well as a mechanistic proposal, are presented.

AB - A highly stereoselective 1,3-dipolar [6+4] cycloaddition towards bridged azabicyclo[4.3.1]decane scaffolds has been developed, reacting aldehydes, 2-aminomalonates and tropone under mild conditions in the presence of a chiral phosphoric acid catalyst. The scope is demonstrated for a series of aldehydes and 2-aminomalonates, and the reaction proceeds in high yields, >95:5 d.r. and up to 99 % ee. A series of transformations, as well as a mechanistic proposal, are presented.

KW - 1,3-dipole

KW - chiral phosphoric acids

KW - enantioselectivity

KW - higher-order cycloadditions

KW - tropone

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DO - 10.1002/chem.202003329

M3 - Journal article

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AN - SCOPUS:85092686527

SN - 0947-6539

VL - 26

SP - 15491

EP - 15496

JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

IS - 67

ER -

Organocatalytic Enantioselective 1,3-Dipolar [6+4] Cycloadditions of Tropone

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