On the roles of protic solvents in imidazolidinone-catalyzed transformations

John B. Brazier; Kevin M. Jones; James A. Platts; Nicholas C.O. Tomkinson

doi:10.1002/anie.201005892

On the roles of protic solvents in imidazolidinone-catalyzed transformations

John B. Brazier, Kevin M. Jones, James A. Platts, Nicholas C.O. Tomkinson

Pure And Applied Chemistry

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

24 Citations (Scopus)

7 Downloads (Pure)

Abstract

The effect of protic solvents on the rate and stereochemical outcome of the imidazolidinone-catalyzed Diels–Alder cycloaddition was rationalized. The following picture emerges: the solvent accelerates iminium ion formation (step 1), the Diels–Alder cycloaddition is reversible (step 2), and the solvent intercepts the iminium ion adduct (step 3).

Original language	English
Pages (from-to)	1613-1616
Number of pages	4
Journal	Angewandte Chemie
Volume	50
Issue number	7
DOIs	https://doi.org/10.1002/anie.201005892
Publication status	Published - 11 Feb 2011

Keywords

Diels–Alder reaction
imidazolidinone
iminium ion catalysis
organocatalysis

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10.1002/anie.201005892

24 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 = "On the roles of protic solvents in imidazolidinone-catalyzed transformations",

abstract = "The effect of protic solvents on the rate and stereochemical outcome of the imidazolidinone-catalyzed Diels–Alder cycloaddition was rationalized. The following picture emerges: the solvent accelerates iminium ion formation (step 1), the Diels–Alder cycloaddition is reversible (step 2), and the solvent intercepts the iminium ion adduct (step 3).",

keywords = "Diels–Alder reaction , imidazolidinone , iminium ion catalysis, organocatalysis",

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AU - Brazier, John B.

AU - Jones, Kevin M.

AU - Platts, James A.

AU - Tomkinson, Nicholas C.O.

PY - 2011/2/11

Y1 - 2011/2/11

N2 - The effect of protic solvents on the rate and stereochemical outcome of the imidazolidinone-catalyzed Diels–Alder cycloaddition was rationalized. The following picture emerges: the solvent accelerates iminium ion formation (step 1), the Diels–Alder cycloaddition is reversible (step 2), and the solvent intercepts the iminium ion adduct (step 3).

AB - The effect of protic solvents on the rate and stereochemical outcome of the imidazolidinone-catalyzed Diels–Alder cycloaddition was rationalized. The following picture emerges: the solvent accelerates iminium ion formation (step 1), the Diels–Alder cycloaddition is reversible (step 2), and the solvent intercepts the iminium ion adduct (step 3).

KW - Diels–Alder reaction

KW - imidazolidinone

KW - iminium ion catalysis

KW - organocatalysis

U2 - 10.1002/anie.201005892

DO - 10.1002/anie.201005892

M3 - Article

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VL - 50

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EP - 1616

JO - Angewandte Chemie

JF - Angewandte Chemie

IS - 7

ER -

On the roles of protic solvents in imidazolidinone-catalyzed transformations

Abstract

Keywords

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Research output

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

Cite this