The modulation of face-face π-π interactions in Lewis acid catalysis

Lisa D. Harris; Robert L. Jenkins; Nicholas C. O. Tomkinson

doi:10.1016/j.tetlet.2005.01.086

The modulation of face-face π-π interactions in Lewis acid catalysis

Lisa D. Harris
, Robert L. Jenkins
, Nicholas C. O. Tomkinson

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

5 Citations (Scopus)

Abstract

The enantiomeric excess obsd. for the exo-adduct from the Lewis acid catalyzed Diels-Alder reaction between cyclopentadiene and methacrolein can be increased up to 21% by simple modification of the electronics of the arom. ring in a series of stilbene-derived diol ligands, suggesting that the proposed face-face π-π interaction between the catalyst and the dienophile can be modulated by altering the electron d. on the arom. ring.

Original language	Undefined/Unknown
Pages (from-to)	1627-1629
Number of pages	3
Journal	Tetrahedron Letters
Volume	46
Issue number	10
DOIs	https://doi.org/10.1016/j.tetlet.2005.01.086
Publication status	Published - 2005

Keywords

methacrolein
dienophile
aromatic rings

Access to Document

10.1016/j.tetlet.2005.01.086

Cite this

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title = "The modulation of face-face π-π interactions in Lewis acid catalysis",

abstract = "The enantiomeric excess obsd. for the exo-adduct from the Lewis acid catalyzed Diels-Alder reaction between cyclopentadiene and methacrolein can be increased up to 21\% by simple modification of the electronics of the arom. ring in a series of stilbene-derived diol ligands, suggesting that the proposed face-face π-π interaction between the catalyst and the dienophile can be modulated by altering the electron d. on the arom. ring.",

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language = "Undefined/Unknown",

volume = "46",

pages = "1627--1629",

journal = "Tetrahedron Letters",

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T1 - The modulation of face-face π-π interactions in Lewis acid catalysis

AU - Harris, Lisa D.

AU - Jenkins, Robert L.

AU - Tomkinson, Nicholas C. O.

PY - 2005

Y1 - 2005

N2 - The enantiomeric excess obsd. for the exo-adduct from the Lewis acid catalyzed Diels-Alder reaction between cyclopentadiene and methacrolein can be increased up to 21% by simple modification of the electronics of the arom. ring in a series of stilbene-derived diol ligands, suggesting that the proposed face-face π-π interaction between the catalyst and the dienophile can be modulated by altering the electron d. on the arom. ring.

AB - The enantiomeric excess obsd. for the exo-adduct from the Lewis acid catalyzed Diels-Alder reaction between cyclopentadiene and methacrolein can be increased up to 21% by simple modification of the electronics of the arom. ring in a series of stilbene-derived diol ligands, suggesting that the proposed face-face π-π interaction between the catalyst and the dienophile can be modulated by altering the electron d. on the arom. ring.

KW - methacrolein

KW - dienophile

KW - aromatic rings

U2 - 10.1016/j.tetlet.2005.01.086

DO - 10.1016/j.tetlet.2005.01.086

M3 - Article

SN - 0040-4039

VL - 46

SP - 1627

EP - 1629

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 10

ER -