Structure activity relationships of secondary amines in iminium ion catalysis

Timothy J. K. Gibbs, Richard L. Elliott, Gareth Evans, Ian L. Jones, 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 are effective catalysts for the asym. iminium ion catalyzed Diels-Alder, 1;3+23; and 1;4+33;-cycloaddns., as well asym. Michael addns. with a range of nucleophiles. We have become interested in developing new catalyst architectures to accelerate this class of transformation to provide more efficient systems than those reported while gaining a intimate understanding of the reaction mechanism. It has been proposed that the rate detg. step of the catalytic cycle is iminium ion formation. Based upon the concept of introducing a heteroatom α- to the reactive nitrogen to increase its nucleophilicity α-effect) we will report on a variety of templates with which we have developed a structure-reactivity relationship model. In conjunction with our synthetic studies we will also report on our theor. and mechanistic findings into the catalytic cycle and the relationship between amine structure and catalyst efficiency. [on SciFinder(R)]
Original languageEnglish
Pages (from-to)ORGN-631
JournalAbstracts of papers - American Chemical Society
Volume234
Publication statusPublished - 19 Aug 2007
Event234th ACS National Meeting of the American Chemical Society - Boston, United States
Duration: 19 Aug 200723 Aug 2007

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Catalysis
Amines
Ions
Catalysts
Nitrogen
Nucleophiles

Keywords

  • structure activity
  • relationships
  • secondary amines
  • iminium ion catalysis

Cite this

Gibbs, T. J. K., Elliott, R. L., Evans, G., Jones, I. L., Platts, J. A., & Tomkinson, N. C. O. (2007). Structure activity relationships of secondary amines in iminium ion catalysis. Abstracts of papers - American Chemical Society, 234, ORGN-631.
Gibbs, Timothy J. K. ; Elliott, Richard L. ; Evans, Gareth ; Jones, Ian L. ; Platts, Jamie A. ; Tomkinson, Nicholas C. O. / Structure activity relationships of secondary amines in iminium ion catalysis. In: Abstracts of papers - American Chemical Society. 2007 ; Vol. 234. pp. ORGN-631.
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Structure activity relationships of secondary amines in iminium ion catalysis. / Gibbs, Timothy J. K.; Elliott, Richard L.; Evans, Gareth; Jones, Ian L.; Platts, Jamie A.; Tomkinson, Nicholas C. O.

In: Abstracts of papers - American Chemical Society, Vol. 234, 19.08.2007, p. ORGN-631.

Research output: Contribution to journalConference Contribution

TY - JOUR

T1 - Structure activity relationships of secondary amines in iminium ion catalysis

AU - Gibbs, Timothy J. K.

AU - Elliott, Richard L.

AU - Evans, Gareth

AU - Jones, Ian L.

AU - Platts, Jamie A.

AU - Tomkinson, Nicholas C. O.

N1 - CAPLUS AN 2007:884598(Conference; Meeting Abstract; Computer Optical Disk)

PY - 2007/8/19

Y1 - 2007/8/19

N2 - Recent reports have shown that the use of cyclic five membered nitrogen contg. heterocycles are effective catalysts for the asym. iminium ion catalyzed Diels-Alder, 1;3+23; and 1;4+33;-cycloaddns., as well asym. Michael addns. with a range of nucleophiles. We have become interested in developing new catalyst architectures to accelerate this class of transformation to provide more efficient systems than those reported while gaining a intimate understanding of the reaction mechanism. It has been proposed that the rate detg. step of the catalytic cycle is iminium ion formation. Based upon the concept of introducing a heteroatom α- to the reactive nitrogen to increase its nucleophilicity α-effect) we will report on a variety of templates with which we have developed a structure-reactivity relationship model. In conjunction with our synthetic studies we will also report on our theor. and mechanistic findings into the catalytic cycle and the relationship between amine structure and catalyst efficiency. [on SciFinder(R)]

AB - Recent reports have shown that the use of cyclic five membered nitrogen contg. heterocycles are effective catalysts for the asym. iminium ion catalyzed Diels-Alder, 1;3+23; and 1;4+33;-cycloaddns., as well asym. Michael addns. with a range of nucleophiles. We have become interested in developing new catalyst architectures to accelerate this class of transformation to provide more efficient systems than those reported while gaining a intimate understanding of the reaction mechanism. It has been proposed that the rate detg. step of the catalytic cycle is iminium ion formation. Based upon the concept of introducing a heteroatom α- to the reactive nitrogen to increase its nucleophilicity α-effect) we will report on a variety of templates with which we have developed a structure-reactivity relationship model. In conjunction with our synthetic studies we will also report on our theor. and mechanistic findings into the catalytic cycle and the relationship between amine structure and catalyst efficiency. [on SciFinder(R)]

KW - structure activity

KW - relationships

KW - secondary amines

KW - iminium ion catalysis

M3 - Conference Contribution

VL - 234

SP - ORGN-631

JO - Abstracts of papers - American Chemical Society

JF - Abstracts of papers - American Chemical Society

SN - 0065-7727

ER -