Iminium ion catalysis: direct comparison of imidazolidinone and diarylprolinol ether reactivity

John B Brazier; Greg P Hopkins; Meriem Jirari; Shaun Mutter; Ronan Pommereuil; Leopold Samulis; James A Platts; Nicholas C.O. Tomkinson

doi:10.1016/j.tetlet.2011.03.129

Iminium ion catalysis: direct comparison of imidazolidinone and diarylprolinol ether reactivity

John B Brazier, Greg P Hopkins, Meriem Jirari, Shaun Mutter, Ronan Pommereuil, Leopold Samulis, James A Platts, Nicholas C.O. Tomkinson

Pure And Applied Chemistry

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

13 Citations (Scopus)

73 Downloads (Pure)

Abstract

Comparison of the relative reactivities of the benchmark catalysts for iminium ion catalysed Diels-Alder cycloaddition under optimised literature conditions showed the imidazolidinone scaffold to possess significantly superior levels of activity in the Diels-Alder cycloaddition when compared to diarylprolinol silyl ethers.

Original language	English
Pages (from-to)	2783-2785
Number of pages	3
Journal	Tetrahedron Letters
Volume	52
Issue number	21
DOIs	https://doi.org/10.1016/j.tetlet.2011.03.129
Publication status	Published - 25 May 2011

Keywords

iminium ion catalysis
imidazolidinone
diarylprolinol ether reactivity
cycloaddition

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10.1016/j.tetlet.2011.03.129

TomkinsonAccepted author manuscript, 318 KB

13 Citations
1 Chapter

Organocatalysed transformations of alpha,beta-unsaturated carbonyl compoundsthrough iminium ion intermediates
Tomkinson, N. & Rowley, J., 14 Nov 2012, Asymmetric Synthesis : More Methods and Applications. Christmann, M. & Brase, S. (eds.). Weinheim, p. 29-34 6 p.
Research output: Chapter in Book/Report/Conference proceeding › Chapter

Cite this

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title = "Iminium ion catalysis: direct comparison of imidazolidinone and diarylprolinol ether reactivity",

abstract = "Comparison of the relative reactivities of the benchmark catalysts for iminium ion catalysed Diels-Alder cycloaddition under optimised literature conditions showed the imidazolidinone scaffold to possess significantly superior levels of activity in the Diels-Alder cycloaddition when compared to diarylprolinol silyl ethers.",

keywords = "iminium ion catalysis, imidazolidinone , diarylprolinol ether reactivity, cycloaddition",

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AU - Brazier, John B

AU - Hopkins, Greg P

AU - Jirari, Meriem

AU - Mutter, Shaun

AU - Pommereuil, Ronan

AU - Samulis, Leopold

AU - Platts, James A

AU - Tomkinson, Nicholas C.O.

PY - 2011/5/25

Y1 - 2011/5/25

N2 - Comparison of the relative reactivities of the benchmark catalysts for iminium ion catalysed Diels-Alder cycloaddition under optimised literature conditions showed the imidazolidinone scaffold to possess significantly superior levels of activity in the Diels-Alder cycloaddition when compared to diarylprolinol silyl ethers.

AB - Comparison of the relative reactivities of the benchmark catalysts for iminium ion catalysed Diels-Alder cycloaddition under optimised literature conditions showed the imidazolidinone scaffold to possess significantly superior levels of activity in the Diels-Alder cycloaddition when compared to diarylprolinol silyl ethers.

KW - iminium ion catalysis

KW - imidazolidinone

KW - diarylprolinol ether reactivity

KW - cycloaddition

U2 - 10.1016/j.tetlet.2011.03.129

DO - 10.1016/j.tetlet.2011.03.129

M3 - Article

SN - 0040-4039

VL - 52

SP - 2783

EP - 2785

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 21

ER -

Iminium ion catalysis: direct comparison of imidazolidinone and diarylprolinol ether reactivity

Abstract

Keywords

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Research output

Organocatalysed transformations of alpha,beta-unsaturated carbonyl compoundsthrough iminium ion intermediates

Cite this