Chemical and theoretical tools for understanding iminium ion catalysis

Timothy J. K. Gibbs, Jamie A. Platts, Nicholas C. O. Tomkinson

Research output: Contribution to journalConference Contribution

Abstract

Recent reports have shown that the use of cyclic five membered nitrogen contg. heterocycles as catalysts for the iminium ion catalyzed Diels-Alder, [3+2] and [4+3]-cycloaddns., as well as Michael addns. of pyrroles, anilines, nitroalkanes, malonates and hydride have met with remarkable levels of asym. induction. We have become interested in developing new catalyst architectures to accelerate this class of transformation with the ultimate aim of providing more efficient systems than those reported. Our approach resides in gaining a fundamental mechanistic understanding of the reaction and applying this knowledge to improve catalytic efficiency. Utilizing a combination of mol. modeling, kinetic investigations and solid-state structural anal. we have probed the catalytic cycle of the iminium ion catalyzed Diels-Alder cycloaddn. reaction. This talk will describe our results in each of these areas and ongoing efforts in using these to develop a predictive tool for catalyst activity in this fascinating class of chem. transformation. [on SciFinder(R)]

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Catalysis
Aniline Compounds
Malonates
Ions
Catalysts
Pyrroles
Aniline
Hydrides
Catalyst activity
Nitrogen
Kinetics

Keywords

  • chemical
  • theoretical tools
  • understanding
  • iminium ion catalysis

Cite this

@article{8646294eb9184eee9b89f3fddf358e8c,
title = "Chemical and theoretical tools for understanding iminium ion catalysis",
abstract = "Recent reports have shown that the use of cyclic five membered nitrogen contg. heterocycles as catalysts for the iminium ion catalyzed Diels-Alder, [3+2] and [4+3]-cycloaddns., as well as Michael addns. of pyrroles, anilines, nitroalkanes, malonates and hydride have met with remarkable levels of asym. induction. We have become interested in developing new catalyst architectures to accelerate this class of transformation with the ultimate aim of providing more efficient systems than those reported. Our approach resides in gaining a fundamental mechanistic understanding of the reaction and applying this knowledge to improve catalytic efficiency. Utilizing a combination of mol. modeling, kinetic investigations and solid-state structural anal. we have probed the catalytic cycle of the iminium ion catalyzed Diels-Alder cycloaddn. reaction. This talk will describe our results in each of these areas and ongoing efforts in using these to develop a predictive tool for catalyst activity in this fascinating class of chem. transformation. [on SciFinder(R)]",
keywords = "chemical, theoretical tools, understanding, iminium ion catalysis",
author = "Gibbs, {Timothy J. K.} and Platts, {Jamie A.} and Tomkinson, {Nicholas C. O.}",
year = "2007",
month = "8",
day = "19",
language = "English",
volume = "234",
pages = "ORGN--396",
journal = "Abstracts of papers - American Chemical Society",
issn = "0065-7727",
publisher = "American Chemical Society",

}

Chemical and theoretical tools for understanding iminium ion catalysis. / Gibbs, Timothy J. K.; Platts, Jamie A.; Tomkinson, Nicholas C. O.

In: Abstracts of papers - American Chemical Society, Vol. 234, 19.08.2007, p. ORGN-396.

Research output: Contribution to journalConference Contribution

TY - JOUR

T1 - Chemical and theoretical tools for understanding iminium ion catalysis

AU - Gibbs, Timothy J. K.

AU - Platts, Jamie A.

AU - Tomkinson, Nicholas C. O.

PY - 2007/8/19

Y1 - 2007/8/19

N2 - Recent reports have shown that the use of cyclic five membered nitrogen contg. heterocycles as catalysts for the iminium ion catalyzed Diels-Alder, [3+2] and [4+3]-cycloaddns., as well as Michael addns. of pyrroles, anilines, nitroalkanes, malonates and hydride have met with remarkable levels of asym. induction. We have become interested in developing new catalyst architectures to accelerate this class of transformation with the ultimate aim of providing more efficient systems than those reported. Our approach resides in gaining a fundamental mechanistic understanding of the reaction and applying this knowledge to improve catalytic efficiency. Utilizing a combination of mol. modeling, kinetic investigations and solid-state structural anal. we have probed the catalytic cycle of the iminium ion catalyzed Diels-Alder cycloaddn. reaction. This talk will describe our results in each of these areas and ongoing efforts in using these to develop a predictive tool for catalyst activity in this fascinating class of chem. transformation. [on SciFinder(R)]

AB - Recent reports have shown that the use of cyclic five membered nitrogen contg. heterocycles as catalysts for the iminium ion catalyzed Diels-Alder, [3+2] and [4+3]-cycloaddns., as well as Michael addns. of pyrroles, anilines, nitroalkanes, malonates and hydride have met with remarkable levels of asym. induction. We have become interested in developing new catalyst architectures to accelerate this class of transformation with the ultimate aim of providing more efficient systems than those reported. Our approach resides in gaining a fundamental mechanistic understanding of the reaction and applying this knowledge to improve catalytic efficiency. Utilizing a combination of mol. modeling, kinetic investigations and solid-state structural anal. we have probed the catalytic cycle of the iminium ion catalyzed Diels-Alder cycloaddn. reaction. This talk will describe our results in each of these areas and ongoing efforts in using these to develop a predictive tool for catalyst activity in this fascinating class of chem. transformation. [on SciFinder(R)]

KW - chemical

KW - theoretical tools

KW - understanding

KW - iminium ion catalysis

M3 - Conference Contribution

VL - 234

SP - ORGN-396

JO - Abstracts of papers - American Chemical Society

T2 - Abstracts of papers - American Chemical Society

JF - Abstracts of papers - American Chemical Society

SN - 0065-7727

ER -