Structural effects in pyrazolidinone-mediated organocatalytic Diels-Alder reactions

Eoin Gould; Tomas Lebl; Alexandra M. Z. Slawin; Mark Reid; Andrew D. Smith

doi:10.1016/j.tet.2010.09.021

Structural effects in pyrazolidinone-mediated organocatalytic Diels-Alder reactions

Eoin Gould, Tomas Lebl, Alexandra M. Z. Slawin, Mark Reid, Andrew D. Smith

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

Abstract

A range of pyrazolidin-3-ones have been prepared and their activity as catalysts for iminium-ion promoted Diels-Alder reactions evaluated. Systematic variation of the C(5)- and N(2)-substituents indicates that the incorporation of an electron withdrawing substitutent at N(2) and either a Ph or CF3 substitution at C(5) results in optimal catalytic activity. The diastereoisomeric resolution of a model C(5)-Ph substituted pyrazolidinone and its ability to impart modest levels of asymmetric induction in the organocatalytic Diels-Alder reaction is also demonstrated. (C) 2010 Elsevier Ltd. All rights reserved.

Original language	English
Pages (from-to)	8992-9008
Number of pages	17
Journal	Tetrahedron
Volume	66
Issue number	46
DOIs	https://doi.org/10.1016/j.tet.2010.09.021
Publication status	Published - 13 Nov 2010

Keywords

IMINIUM ION CATALYSIS
C-CARBOXYL TRANSFER
ORGANIC CATALYSIS
AZOMETHINE IMINES
O-CARBOXYL
ACCELERATION
DERIVATIVES
STRATEGIES
CARBONATES
HYDRAZINES

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10.1016/j.tet.2010.09.021

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title = "Structural effects in pyrazolidinone-mediated organocatalytic Diels-Alder reactions",

abstract = "A range of pyrazolidin-3-ones have been prepared and their activity as catalysts for iminium-ion promoted Diels-Alder reactions evaluated. Systematic variation of the C(5)- and N(2)-substituents indicates that the incorporation of an electron withdrawing substitutent at N(2) and either a Ph or CF3 substitution at C(5) results in optimal catalytic activity. The diastereoisomeric resolution of a model C(5)-Ph substituted pyrazolidinone and its ability to impart modest levels of asymmetric induction in the organocatalytic Diels-Alder reaction is also demonstrated. (C) 2010 Elsevier Ltd. All rights reserved.",

keywords = "IMINIUM ION CATALYSIS, C-CARBOXYL TRANSFER, ORGANIC CATALYSIS, AZOMETHINE IMINES, O-CARBOXYL, ACCELERATION, DERIVATIVES, STRATEGIES, CARBONATES, HYDRAZINES",

author = "Eoin Gould and Tomas Lebl and Slawin, {Alexandra M. Z.} and Mark Reid and Smith, {Andrew D.}",

year = "2010",

month = nov,

day = "13",

doi = "10.1016/j.tet.2010.09.021",

language = "English",

volume = "66",

pages = "8992--9008",

journal = "Tetrahedron",

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publisher = "Elsevier",

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TY - JOUR

T1 - Structural effects in pyrazolidinone-mediated organocatalytic Diels-Alder reactions

AU - Gould, Eoin

AU - Lebl, Tomas

AU - Slawin, Alexandra M. Z.

AU - Reid, Mark

AU - Smith, Andrew D.

PY - 2010/11/13

Y1 - 2010/11/13

N2 - A range of pyrazolidin-3-ones have been prepared and their activity as catalysts for iminium-ion promoted Diels-Alder reactions evaluated. Systematic variation of the C(5)- and N(2)-substituents indicates that the incorporation of an electron withdrawing substitutent at N(2) and either a Ph or CF3 substitution at C(5) results in optimal catalytic activity. The diastereoisomeric resolution of a model C(5)-Ph substituted pyrazolidinone and its ability to impart modest levels of asymmetric induction in the organocatalytic Diels-Alder reaction is also demonstrated. (C) 2010 Elsevier Ltd. All rights reserved.

AB - A range of pyrazolidin-3-ones have been prepared and their activity as catalysts for iminium-ion promoted Diels-Alder reactions evaluated. Systematic variation of the C(5)- and N(2)-substituents indicates that the incorporation of an electron withdrawing substitutent at N(2) and either a Ph or CF3 substitution at C(5) results in optimal catalytic activity. The diastereoisomeric resolution of a model C(5)-Ph substituted pyrazolidinone and its ability to impart modest levels of asymmetric induction in the organocatalytic Diels-Alder reaction is also demonstrated. (C) 2010 Elsevier Ltd. All rights reserved.

KW - IMINIUM ION CATALYSIS

KW - C-CARBOXYL TRANSFER

KW - ORGANIC CATALYSIS

KW - AZOMETHINE IMINES

KW - O-CARBOXYL

KW - ACCELERATION

KW - DERIVATIVES

KW - STRATEGIES

KW - CARBONATES

KW - HYDRAZINES

U2 - 10.1016/j.tet.2010.09.021

DO - 10.1016/j.tet.2010.09.021

M3 - Article

SN - 0040-4020

VL - 66

SP - 8992

EP - 9008

JO - Tetrahedron

JF - Tetrahedron

IS - 46

ER -

Structural effects in pyrazolidinone-mediated organocatalytic Diels-Alder reactions

Abstract

Keywords

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